


Life is anything but fair

by merrythoughts, ReallyMissCoffee



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Angst, Bottom Dean Winchester, Canon events still happen, Dirty Talk, Episode: s05e22 Swan Song, First Time, Guilt, M/M, Porn with Feelings, Rimming, Roleplay Logs, Top Sam Winchester
Language: English
Status: Completed
Published: 2019-02-08
Updated: 2019-02-08
Packaged: 2019-10-24 06:17:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 26,776
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17699207
Author URL: https://archiveofourown.org/users/merrythoughts/pseuds/merrythoughts, https://archiveofourown.org/users/ReallyMissCoffee/pseuds/ReallyMissCoffee
Summary: It's a cowardly thing to be doing because Sam won't have to face the consequences of this. Dean will have to. Dean will have to live each day knowing how messed up his younger brother really was. Sam's pretty sure he wouldn't have started shit if tomorrow wasn't happening. Sam's held out this long. He's behaved about this one thing (at least). If he wasn't booking a one-way trip to Lucifer's cage, he'd have kept on behaving. He'd inherited the Winchester repression, after all.





	Life is anything but fair

**Author's Note:**

> Started in 2017, re-found it, and finished it in 2019! Hurrah. Apparently we excel at writing first time one-shot angsty porn for Supernatural...
> 
>  **Disclaimer** : This is another merrythoughts & ReallyMissCoffee production. In case you don't know us, just a heads up: this is written first and foremost as an alternating roleplay between us which doesn't necessarily translate smoothly into an easily digestible or traditional fic format. At times we can be pretentious, repetitive and annoyingly wordy, but we're not going to change so please forgo any "constructive criticism" regarding the format. We are choosing to share our work and if you like it, you like it, if not, press the back button and try something else as we have no interest in attempting to fic-ify our stories.
> 
> Sam written by Merry ([tumblr](http://merrythought.tumblr.com)) | Dean written by ReallyMissCoffee ([tumblr](http://reallymisscoffee.tumblr.com))

They finally have a real shot at stopping the mess that he's started. Sure, he's not going to make it -- but hey, Winchesters finish what they start. This is his responsibility and he's going to damn well make sure he gets Lucifer back into the cage. It's the least he can do for getting him out.

Sam knows he hasn't made the best decisions in his life. A part of him wants to argue that having John for a father and Dean for a brother had contributed to this particular handicap. After all, it seemed like Dean's sole mission was to try and _save_ _him_ at times and that led to certain patterns repeating themselves. Having an overbearing older brother... Well, it took its toll in ways. Sam's always been used to Dean weighing in on his decisions and getting an earful of Dean's opinions. He's also been used to Dean pulling him out of scraps and having his back no matter what. And when Dean had been gone - in Hell because of him - Sam had really gone off the rails. 

Directionless. Dean-less. He would have given anything to hear Dean's disapproving tone or lame jokes. (He wouldn't change Dean for the world even though he knows he's absolutely not good for Dean.)

Because Sam knows there's a darkness deep in him. Is it even the blood Azazel fed him, or has he been flawed since conception? He's always been different, even within his own family. He can remember Dean's expression while faced with Sam's "good memories" in Heaven... There's a shitty rebellious part of himself that _still_ craves the demon blood, that still wants to be strong and thinks he can control it. (When will he learn his lesson? Wasn't he supposed to be the smart one? Well, Sam will find out soon enough because he'll be gulping it down when they get to Detroit.)

They're on their way to Detroit now, stopped over in a motel for the night. Bobby is shacking up in a room with Cas and Sam's with Dean as per usual. Sam can tell Dean is still awake. Night after night sharing rooms across the country, yeah he knows how his brother can remain motionless while waiting for _him_ to fall asleep first (not that he blames Dean, Sam had snuck off plenty of times to hook up with Ruby). So, Sam doesn't bat an eye as he gets off his own bed and comes to sit on the end of Dean's. 

"Hey, Dean..." Sam murmurs.

* * *

_'What are you afraid of? Losing, or losing your brother?'_

His brother. Dean knows the answer right down to his soul, but like this, in a crappy motel a few miles outside of Detroit, it doesn't matter. Sam might be saying _yes_ but Dean is the one who's given the go-ahead. He'd green-lighted the whole goddamned thing because Bobby is right. This is their best shot, and if they don't do it, millions - maybe billions - of people will die. 

Dean only wishes the numbers made any difference. A million people? Five million? Ten? All compared to Sam. It's no contest, which is why Dean had said yes. He's willing to put the lives of half the population of Earth at risk just because he can't stand the thought of losing Sam.

They'd stopped in at a motel a good four hours ago for a final night to rest up before the big confrontation. There's demon blood in the Impala's trunk and the Horsemen's rings are burning a hole in Dean's pocket as he stares up at the ceiling. Cas and Bobby have their own room, and Dean should be sleeping, but he's not. Sam is awake, and as horrible as it is, he wants to remember this. He's living on borrowed time now. Sam might be the one who's going to end in a few hours, but Dean's the one who's got to live without him after. Ideally, they both die. He could handle that. At least then he'd be with Sam, maybe be able to keep him safe. Hell terrifies Dean, but he'd go in a heartbeat if it meant helping Sam.

There's an old clock ticking on the wall, the sound tinny and ancient, and the room smells of cheap cleaner and old greasy fast food wrappers. Dean stares at the ceiling, his arms crossed, and when Sam stirs on the bed beside him, he draws in a deep breath and holds it, blinking back the crazy urge to break down and beg. He's always known he needs Sam more than Sam needs him. This - willingly walking his brother to die because it's the _right_ thing to do - is the hardest thing he's ever done.

Sam comes over and sits on the edge of his bed and Dean fights back the burning behind his eyes and in his throat. He chokes on a million things to say, Death be damned. ' _Don't do it_ ', ' _please_ ,' ' _I need you_ ', ' _we can find another way_ '. 

Instead he works his jaw until it aches, and manages, "hey, Sammy." It even sounds almost solid. "You should... you should be asleep."

* * *

This time he's gotta clean up the mess, not Dean. Sam knows this. Dean must know it too as he's finally (reluctantly) given his OK on the plan. He's still scared. Sam wants to believe he's strong enough to take back control from Lucifer and do what needs to be done… but isn't his _weakness_ the very thing that gets him into most, if not all, of these problems to begin with? There's no guarantee he'll be strong enough to do the right thing, but everyone is counting on him to set things right, so he has to.

Dean has been trying to protect him as early as Sam can remember. He may be sick and tired of the classic rock, but next to his brother in the Impala… God, he'd give anything for them to turn around and drive away from all of this with the stereo blasting. Dean would probably do it too because Dean went to Hell for him. How does someone process that? They don't because it's too much to handle. It aches in Sam's chest. Blood... Family… Sometimes it all feels like ropes pulling tighter around him. After all, he couldn't ever escape the hunter lifestyle and with him back in it… well, he'd made a right mess of everything. The silver lining of this plan is that, with him out of commission, he can't get into any more trouble. (This isn't something he will ever voice, but it's still there.)

This is his last night as himself inside his own body and Sam can't help but gravitate to the single most important and influential person in his life. 

"So should you," Sam points out. He runs a hand through his hair. Dean had been willing to say yes to Michael and still held it together... He's not Dean though. Dean is stronger than him. 

Screw it. He needs his big brother right now. This is his last night as himself on Earth, he's not going to pretend to be all macho and all right. (He's been far from all right for a while now.) So Sam crawls up on the bed and lies next to Dean, curling into him. 

"Shut up. I know it'll be a stretch but pretend like I'm five or something." They're both not big on showing vulnerability, but Sam doesn't think Dean will push him away. Not tonight.

* * *

Dean wants to take a walk. He wants to punch something, to take a crowbar to car windows, to beat the Hell out of something until it stops moving. He has so much inside of him that it's suffocating, but the screams in his mind eventually only coalesce into one name: _Sam_. 

Dean's worried for everyone. He hates that Bobby is coming along. He hates that he's fucked up Castiel's life and dragged him into this, but he's grateful for the support, for the help. But beyond all that, everything is simple. Dean would give anything to turn around, to drive away, to leave. He wants to pick it all up and burn it all down, and he can't. He's painfully, impotently just one man, and with every breath he takes, he's failing the one rule he's lived by all his life: Keep Sam Safe.

Sam points out his hypocrisy and Dean mirthlessly lets out a breath of a would-be laugh that comes out as a soft, "yeah." It's clear he doesn't intend to get any sleep regardless. Instead he just lays there, tapping his thumbs against his biceps from where his arms are crossed. Everything inside is telling him to talk, but the impulse zips from his brain to his mouth and Dean... he's got nothing. He's already made his promises. Lisa. Don't try to break the cage. He closes his eyes and swallows down the despair inside and it chokes him.

So when the bed suddenly dips and the double - _way_ too small for two six-foot-plus men - creaks under him alarmingly, Dean jolts. He's all set to grumble, to shove, but then reality strikes him again. Dean stills, and as Sam curls up by his side, he doesn't need to _pretend_ like Sam is five. That twist of agony grows and Dean has to try three times to swallow as Sam's warmth curls in against his side. It's been ages since they'd done this, but all of Dean's protests about Sam being a girl or 'wuving hugs' don't even make it to his lips. Instead he watches and, after not even a few seconds, Dean unwinds his arms. 

He reaches down and - without looking at him - he winds an arm around Sam's shoulders and draws him in closer. Sam's bigger than he is. He's way too big to use Dean's shoulder as a pillow the way he once had, or to curl up on Dean's chest during long car rides, but Dean pulls him in like Sam is still a kid. He doesn't hesitate to press his cheek to the top of Sam's head, staring fixedly ahead like his world is crashing. It is. But while Dean can sometimes share his concerns with Castiel - or he could - Sam is different. Dean's always looked out for him, and if Dean's afraid then Sam... He can't help but want to fix it. 

"You know... I always used to tell you to get a freakin' haircut, but I'm kind of glad you didn't now. Before you shove the Devil back into the passenger's seat, he's gonna have to come to grips with the fact he's got hair out of a Herbal Essences commercial."

* * *

He knows Dean is less about _showing_ comfort and more about kicking down doors and solving problems with a gun. A quick hug is one thing, but this isn't a 'good to see you, man' or 'thank God you're safe' thing. This is pretty much cuddling, him seeking comfort and shelter… Dean loathes the touchy-feely crap (talking about feelings? What's that?) but Dean has always been there for him, so Sam knows Dean isn't going to shove him away. No matter how much he screws up, his brother hasn't ditched him. (That rope tightens.)

Dean doesn't shove him away. A few seconds pass before Dean is moving and welcoming him _home_. And in Dean's arms, it does feel like a familiar home. Yeah, maybe it's sappy (okay, it is) but Dean has been the _one_ constant in his life. It's at least been over a decade since Dean's comforted him from nightmares or pulled him close in the backseat of the Impala, but his body still remembers this.

Sam wiggles his way closer, his head coming to rest on Dean's chest and his arm draping over Dean's stomach. Dean is no wimp himself, and there's no soft curves to greet him. There's just muscle and firmness, but it's _Dean_ and their shared aftershave and deodorant. Home personified in a body (albeit a smaller body than his own, but that's fine).

And then Dean cracks a joke. Of course, Dean does. Sam scoffs softly. This is also familiar. He's probably scaring Dean with all this mushy clinging, but Sam can't help it. He wants to be close with someone tonight and why shouldn't it be Dean? Dean's been a part of every major thing that's happened in his life so it stands to reason that Dean should be involved in the end of it. 

"Sadly my glorious mane is probably the only good thing I got goin' for me," Sam comments. He shuts his eyes and sighs. He's going to miss his brother. He just hopes Dean can leave him behind and start over with Lisa.

* * *

"It's not even that good," Dean mutters, because this is what they've always done. He's always been Sam's shelter in the storm and he's always needed Sam just as much. He teases him and Sam teases him back. They bicker, they sometimes fight, but it's always just them against the world. Back to back, guns blazing, always having each other's backs'... Without Sam, his life has no purpose. He'll have Bobby and he might have Cas if he sticks around, but he won't have his brother. What's the point without Sam? 

The thought strikes him hard enough that his heart skips alarmingly and that tightness in his throat just climbs higher. He doesn't clear his throat, but it's a close thing. Instead Dean pulls Sam closer and locks away every part of this, all the way down to the scratch of Sam's five o'clock shadow poking him through the thin cotton of his black t-shirt. It's new. They haven't done this since they were kids, and Dean is suddenly filled with a desperate thought. _Why not?_ Why hadn't they done this? Why had he let his goddamn pride-- ...

But his regrets and his desperation aren't what Sam needs now. Dean breathes in slow and watches as Sam's head lifts a little in response. Dean's palm splays wide over Sam's back and he holds him the way he always did in the past. The way that says 'it'll be okay, Sammy. I've got you.' Right now, Sam needs him in more ways than he can handle, which is precisely why Dean sucks it the fuck up. 

"But come on, I'll bet you a couple hundred you got more goin' for you than you think. I bet there are a few ladies who'd agree with me." Dean reaches up to lightly muss Sam's hair, but the touch lingers. He can joke, but he doesn't want to draw back. "And trust me, I don't think they're after your _mop_."

* * *

They've been through a lot together. Christ, they've both _died_ , so what's one more on the list for him? If they can't kill Lucifer with the Colt, shoving him back in the cage is the next best thing and Sam knows Lucifer isn't going to be exactly happy about this plan. (Every night Sam closes his eyes, he wonders if he'll see Lucifer-in-Jess again... if he'll have to hear Lucifer try and spin his words and experience the easy-going nonchalance coupled with the _honesty_.)

Sam feels the comforting touch of his brother's hand on his back. So familiar, but the hand is much larger than it had been last time. Sam's pretty sure other siblings don't lie like this as their age, but then again, they're not like most siblings. They're brothers who are meant to fight to the death as vessels for squabbling angel brothers. There's nothing normal about them. So who cares if he's going to be baby and cling onto Dean. 

Dean's use of humor... Sam wants to rise to it, wants to pretend he can joke around and be fine, but he's far from fine. They both are, but Dean has always been better at putting on a brave front. Sam tries though. He has the best to learn from, right? Like older brother, like younger brother--

Sam lets out a small derisive chuckle out. He has to try at least. "End of days here, you shouldn't be playing fast and loose with your cash," Sam cautions. "Going to be harder to hustle pool without me." Sam's voice is softer at the end of his statement. It's true, but it sucks. For whatever reason, he pushes his head against Dean's fingers that have stayed in his hair.

* * *

Dean is trying because he has to. Because there's no other choice. The alternative would be taking back his word, would be grabbing Sam and shanghaiing him as far away from this mess as is possible. Dean's considering it with every breath he takes. Why does it have to always be them to sacrifice? Why does everything have to be on their shoulders? Sam's still basically a kid. This shouldn't be on him. And yet he's also an adult and Dean had given his word.

Humor is all he's got. Without it, the urge to grab Sam and run or start begging him to reconsider rear up within. And so when Sam's response lacks the humor and instead has too much reality stabbed into it, Dean goes quiet. He freezes just enough to be noticeable and immediately the wry smile he'd managed to piece together crumbles. The sudden ache in his chest is violent and vicious and Dean's throat feels about five sizes too small. He focuses all his effort on swallowing past the lump in his throat and only half manages. Instead he lets out a soft, breathless, "Yeah," and everything inside him tries to scream at the idea that he's allowing this.

The begging comes back in his head but Dean fights it back down. He considers the position and decides that he doesn't care if Sam is too old for this. He thread his fingers through Sam's hair and keeps them there, curled and just shy of desperate. His hands say everything he's not willing to. They say _please_ and _don't go_ and _this isn't on you._

But mostly they _say this isn't fair_.

Dean can't force a smile. He tries but all it results in is an awkward tremble of his jaw that goes nowhere. "Yeah, I guess it is." Dean's voice sounds scraped raw, and he suddenly wraps his arm around Sam a little tighter and pulls him in close like if he lets go, that's it. Sam is dead. It's how he feels.

* * *

It's the right thing to do. No, it's the _only_ thing to do. That doesn't make it any easier for Sam to stomach. He's resigned to his fate though. Cleaning up messes... it's usually Dean's job, but this one is on him. This is the biggest mess he's ever made. Looking back... God, it's a bitter pill to swallow. All of his good _intentions_ polluted by Ruby. And he should have known better, but Sam had felt at the end of his rope with Dean gone... But what was his excuse when Dean _came_ _back?_

Sam doesn't like remembering about him slipping out of motel rooms late at night, of the lies he told Dean. (Of believing Dean wasn't strong enough to get the job done, but _he_ was.) It had been enough for Dean to want to split ways with him. The end of the brothers working together.

Thankfully it hadn't lasted. The only thing worse than facing the apocalypse would have been facing it without his brother by his side. But Dean is with him and Dean gets the hint because he strokes his hand through his hair and Sam sighs at the sensation. It feels _good_. Yeah, it's not a woman, but he's never been all that concerned with trying to prove anything. Some things are bigger and more important than _looks_ and what's considered normal. Dean is one of them.

Dean has always been one of them. And when Dean replies, Sam can tell there's emotions working through his brother. An arm tightening around him feels like a noose around his heart and Sam shifts closer, pressing into Dean and wanting to imprint this memory on his brain. The feel of Dean holding him. Dean not giving up on him. Dean trusting him even though he has very little reason to. 

"I'm here," Sam says. And he may be bigger than his brother, but Dean's always managed to be his shelter so Sam lifts his head up and forcibly nuzzles into the side of Dean's neck. 

He inhales deeply. It's home. It's Dean.

* * *

Dean is trying to keep it together but he already knows he'll fail. He can feel his eyes burning the way he'd never let himself feel in front of anyone but Sam. The few times he's let the wall down around Cas or Bobby, it's been shameful. With Sam... yeah, he still feels ashamed, but he knows Sam won't say anything. Sam knows him. Dean doesn't think there's many people who know him as well as Sam does. So he doesn't kid himself in this. He knows Sam can feel his grief. He knows this is too much for the both of them. But Sam doesn't pull back, and Dean doesn't let him.

Dean holds him instead, and when Sam correctly reads the tension in Dean's voice enough to whisper his soft reassurance, Dean only wishes it was enough. But even as Sam lifts his head from Dean's chest to instead press his face in against his neck, all Dean can think is 'yeah, but for how long?' He doesn't have the hope some people do, that loved ones stick around after death. He knows what's waiting for Sam, and it's murder to just let him walk into slaughter. No, more than that, he's _leading_ him to slaughter, willingly.

Dean feels Sam's ridiculous hair press in against his chin and the first tear cuts a hot path down his face. Dean blinks hard and wills more to stay away, but he can't stop the slightly tremulous way he turns his head, just enough to press his lips to Sam's forehead. He hasn't given affection like this since they were really young, but that doesn't mean he hasn't wanted to. They're grown ass men; men don't do this. But given the circumstances, Dean throws all his preconceived notions out of the window and instead grips hard at Sam's back, holding him as close as he possibly can. 

"Yeah, I know you are," Dean says, and fuck, yeah, his voice is shot. The desire to beg is almost overwhelming and he only just manages to swallow it down. "We'll... we'll see this through. It's gonna be okay, Sammy." He doesn't believe it, but he has to say it. For Sam's sake.

* * *

Dean is going to have trouble with this. Sam knows it. Dean doesn't deal well with loss, with problems he can't face head-on and kick the crap out of. And that's why Sam had made Dean promise: no messing around with the cage. No more deals. Lisa and Ben. A normal life -- something Sam's always wanted, something he had run away from his own family for... And maybe he's shoving his dream at Dean, backing Dean into it... But Dean has never been good at taking care of himself. A family life will be good for him. Dean will be a good father; Sam knows because Dean practically raised him.

(Maybe he didn't turn out the best, but he's certain Ben is going to. Lisa and Ben have a real chance of helping Dean. He'd been cursed, he'd been hopeless. Dean hadn't failed him.)

Sam knows Dean is crying. He knows from the slight tremor. He knows, he knows, he knows. This might tear Dean apart. This might be too much for him to bear, but Sam has no choice. He started this, he's got to finish it. He's not going risk anyone else's life for his mistakes. 

Dean holds onto him tightly. The compression barely registers with Sam. And with a voice that has very little conviction, Dean lies and tells him it will be okay. "'course we will," is all Sam can grit out, his own voice tight.

 

He doesn't like this. He doesn't like this at all and it's his damn fault. Sam isn't really thinking when he kisses Dean's neck. He just does it. And then he repeats it, his mouth dry. Since Jess, anything romantic or sex-related has been mostly done as an outlet, as a distraction or as a bid for power. This… this isn't that.

* * *

How much of him will be left after this? How much of _Dean Winchester_ relies on Sam being okay? If Sam is gone, if Sam is suffering eternally in Hell, how will Dean manage? He can't even think about it right now because if he does, he swears he'll find Death again and risk killing him just for a chance at joining Sam in the cage. If Dean jumps in too, will anyone mind? Two versus one. Maybe... just maybe, he can protect Sam in the cage too, but Dean doesn't know how it works. He doesn't know what to do, and he hates that he doesn't.

So instead he holds Sam tight enough to hurt and focuses on each breath. He locks this moment away, the warmth, the comfort, the flare of desperation, everything. Dean doesn't want to forget this because he thinks he'll be living in this moment for a long time after, if he lives at all. 

He's focused enough to hardly register it when Sam's lips find his neck. Dean startles after a moment though, because that's new. It's a quick heat, dry and with the slight scratch of stubble, and Dean's anguish fades just enough to be confused. It's when Sam repeats it that something flares inside. Confusion and alarm and about seven helpings of _more_ confusion crash in on him, but despite it all, Dean doesn't draw away. 

He can't. Whatever this is, it's Sam. Right now Dean doubts he'd care were Sam to cut him open and rip his heart out. It can't be worse than the feeling he has now. So a kiss, albeit one that seems more weighted than most hardly flickers his needle. Maybe it's all Sam can reach, but a small voice in the back of Dean's mind doesn't think so. 

"Sam?" Dean asks anyway, confused but not resistant. He's just too beaten down to care.

* * *

Later, Sam will probably count this as just another quintessential Sam Winchester mistake -- another incident of bad decision making on his part, but right now, he's running on nerves and desperation. He doesn't know what his aim is. He probably doesn't have one other than to somehow act and _do something_. Maybe he's looking for a distraction. Maybe he's looking to try and comfort Dean... Can he even help Dean? 

Sam doesn't know. Sam knows he's gotta say 'yes' and get Lucifer in the damn cage. That's all he knows, but the rest of it... Saying goodbye to Bobby and Cas? Knowing this is his last night as himself and on Earth? How does someone deal? He's signing up for eternal torture with two 'angel dicks' as Dean would call 'em.

Apparently, he deals by proving once again that he's a freak and kissing Dean's neck. Proving that there's something fundamentally wrong with him. Something flawed. Something Dean has tried hard to correct and do damage control for (to no avail). Dean doesn't even push away and it's in this instant, hearing the confusion and resignation, Sam knows Dean is honestly too defeated to even try and stop him.

And Sam's not strong enough to say no to his urges, to the desperation and craving for comfort in any way possible. Dean is all he has. So Sam's head lifts off and he glances up at his brother's face. He can see the faint wetness of a tear. 

"I'm sorry for this," Sam murmurs and he's hoisting himself up, climbing on top of Dean, coming to straddle him and his hands coming to hold Dean's face still as he leans in and kisses Dean properly.

* * *

Were Dean to look at it properly, Sam's actions would make sense. In a way, they do, but he's so broken down over what he's decided that he can't find it in himself to even begin to think about why they shouldn't. He doesn't know for sure, though, and Dean... he'd push. He'd do this in a heartbeat if he _knew_ it was what Sam wanted, but he can't do anything to fuck up this last night. If he fucks it up, if he ruins this last day with Sam, he'll never forgive himself. So Dean waits and he lets Sam draw back.

He watches quietly as Sam glances up at him and Dean immediately tries (and fails) to school his expression into something more put together. He wants to look like he's in control. He wants to protect Sam, wants to be brave for him, but he can't. Dean's only ever been afraid of one thing: losing Sam. He's got Castiel now, and he's got Bobby, but... it's _Sam_ on the chopping block, and he can't pretend he's okay.

So when Sam apologizes, Dean looks even more confused, and then he's just left in stunned disbelief as Sam rises from his arms. Dean stays still as Sam throws long legs over his hips and his hands (fuck, his hands are big; Dean never noticed) come to rest on Dean's face. He knows then, but he still doesn't _know_ until Sam leans in, and then something in Dean's mind just crumbles. 

Sam's lips are soft, and this is so many counts of fucked up and wrong, but it doesn't feel like it. It feels like closeness. It feels so viscerally stunning that there's no way he'll ever forget this moment, or the muffled sound of surprise he makes that fades into something just shy of desperate. Dean's mind sets up token protests. He's not gay. They're brothers. What would Dad say? What would Bobby or Cas think? But every protest just crumbles to dust.

It still takes Dean a few moments to adjust. Sam's no chick. He's big, and he's heavy, and he's strong, but he's still Dean's little brother, and if this is what Sam needs for comfort... Dean's not a big enough man to ruin this. So he reaches up and threads his fingers through Sam's hair and kisses him back almost haltingly. It's warmth and intimacy and Dean chases it, and for a moment he wonders which of them really needs this.

* * *

He's never really thought of doing this before, he's not that much of a freak. Sam doesn't even know what this _is_ exactly... It's him on top of Dean, it's his hands cradling Dean's face and it's his mouth on Dean's own. He understands what he's doing, he's just a little foggy on the details of _why_. (This doesn't seem like something he should look into.)

He's going away. He's going to Hell. With Michael and Lucifer. He's going to suffer and he's going to leave everyone he loves behind... But are those good enough reasons to be doing _this_? Sam's not an idiot, he knows this isn't at all normal and it just cements the fact that _he_ isn't normal. He's putting the moves on his fucking _brother_ for God's sake and Dean is just destroyed enough to let him.

But it's _Dean_ and Sam aches to be close and physical and to feel something other than grief and loss and fear. Dean's hands are back in his hair and Sam makes a sound of approval at it as fingers stroke. He kisses Dean with short clipped kisses that keep Dean guessing as he pulls away and then presses back in. Sam has had a few college experiences with other guys, but this is something completely different. This is Dean and it means more than Sam can put into words. He licks at Dean's lips, his hands smooth down Dean's neck as he purposefully grinds into Dean's crotch.

Sure, a part of him is mortified that he's doing this, but it pales in comparison to the gnawing ache inside his chest.

* * *

Were it any other night under any other circumstance, Dean would be shoving Sam away with a bitten-off, 'dude what the fuck!' Tonight isn't any other night, though. Tonight is a night where Dean wishes he could just press pause on the world. A night where he wishes he could grab Sam and run, or meld so completely together that even in the pit, they wouldn't be separated. He can't protect Sam from topside, which is precisely why Sam made him promise. Sam knows him. Sometimes Dean thinks Sam knows him better than Dean knows himself.

So yeah, this is fucked, but it's _their_ fucked. Dean doesn't struggle. He doesn't shove away or turn his head or anything he _should_ do. Instead one hand grips and strokes through Sam's hair and the other moves around to grab tight at the back of his shirt, yanking him in closer, keeping him there. He's never done this before; he's never even thought about it, so ultimately Dean has no idea what to expect. He walked in on Sam making out with a girl in middle school once, but it hadn't been like this. Sam's picked up a few things since then.

Each kiss is a tease, leaving him wondering when the next will come, and it's so fucking _Sam_ that he almost laughs. Always looking to stir the pot. Always looking to think outside the box. Well... this is about as far outside as they can get. So Dean kisses back when he can react quick enough, and he curses under his breath at the pointed grind before another kiss silences him. He'll remember this, and that's what's important. 

"It's okay, Sam," Dean says between slightly-breathless kisses. "This is okay. You're okay."

Dean knows Sam. He knows what this _could_ do if he gives it the chance to, so he won't. Dean doesn't care if this is new or old. He doesn't care about much now outside of each press of Sam's lips and the heat rushing belatedly to his dick. So he strokes Sam's hair. He clutches him closer. He grabs at Sam's shirt and then abandons it, yanking up the back of Sam's shirt so that he can slide his arm under instead and splay his hand against bare skin, nails digging in just enough to feel.

* * *

God, he's messed up. _This_ is messed up, but Sam knows he's not going to stop. He can't stop. This is his last night in his body, as himself, and he's scared and this is apparently what his freak self wants to delve into.

There's no denying this his brother is attractive. Sam would have to be blind to not notice the appreciative glances Dean gets. But this isn't about _his_ attraction. Sam's mostly straight, or at least heteroflexible? Was that what the kids called it in college? But Dean eclipses everything at this moment. Dean shakes it all up and Sam is grasping at anything familiar right now.

Dean kisses him back and it's honestly _nice_. Dean's lips are full and warm, a fit body underneath his is also nice. Arousal jolts through Sam as Dean reassures him. It's exactly what he needs to hear. Dean accepts him, Dean is okay with him -- with this.

Sam let's himself groan as one of Dean's hands scrambles underneath his shirt, the touch causing shivers as nails dig into his back. Sam bites at Dean's bottom lip before taking it in and sucking. He rocks against Dean, not embarrassed that he's already hard in his boxers. Dean both feels new and familiar. Sam pulls away from Dean's mouth, gasping out his brother's name before he ducks back and bites at Dean's neck. They're quick nips as his hands roam down Dean's arms, taking in their strength, one even running down Castiel's mark.

* * *

It's a measure of how fucked up their lives are that when Dean hears Sam groan, immediately he's on guard before he realizes that it's not a groan of pain. He's not okay. None of what they're planning is okay. But this is fine. This is bordering on good. It's not Dean breaking down into a soulless heap at the thought of his brother gone and so he focuses as hard as he can on every single second of this fucked-up encounter. Sam is as familiar to him as his own body, maybe more so. No, _definitely_ more familiar. Dean's stitched up Sam's skin and held him tight. He's cooked him meals and taken the brunt of whatever he could. He's sacrificed meals so Sam could eat, had given his life so Sam could live... Sam's familiar to him.

So that there's a part of his brother that he doesn't know is something else. Dean isn't sure if he likes it, but it doesn't matter. Sam's fixing it anyway, and once Dean realizes that Sam isn't in pain, the groan really registers and Dean presses his nails to Sam's skin again, correctly reading that it had been the cause. He has a moment to wonder, to marvel, and then Sam's leaning in and kissing him again. The bite to his bottom lip followed by the suck has _Dean_ groaning, his hips lifting into the rhythm Sam's set. 

He's no slouch in the bedroom. He knows how to please. If this is what Sam needs, Dean's going to do whatever he can to please him too. With Sam's gasp of his name still ringing in his ears, Dean tilts his head to let Sam in close, feeling the quick nips along his throat that he curses at. When Sam's hand brushes the handprint mark on his shoulder, Dean's gut twists a little in guilt, but that's all it is. It's a momentary flash that's gone the next minute, and Dean focuses instead on clutching Sam closer.

There's hardly room for one grown-ass man on the bed let alone two, so Dean does what he can to steady Sam. His breathing is rougher as he starts getting hard (which is a miracle considering how empty Dean feels) and every time he can formulate words, he does. 

He only says little things. Things like: "that's it, Sammy," or "fuck, that's good," or "god, do that again," and in their little pocket of the universe where Dean wishes time would stand still, he's almost - _almost_ \- able to pretend that his world isn't going to end in under 24 hours.

* * *

It's wrong, sure, but his very existence feels wrong. If he hadn't... God, that list is too long. Sam doesn't want to go down that road. So, he chooses to go down this one. He's perverting their bond, pulling Dean down into his darkness, but Sam can't handle being alone. The idea of stopping, climbing off Dean and returning to his own bed? The distance feels like too much to handle. How could he sleep alone in another shitty hotel bed?

If this is his last night, he'll let himself be selfish (even if it's so very wrong) and maybe in the process he'll show Dean just what kind of freak he really is... Maybe Dean will finally realize that he is better off without him. Dean deserves that apple pie life, he deserves a woman who will cherish and try and take care of him for a change. Sam's stolen so many years, it's time to let him go.

But he doesn't let go now. He _takes_ and he learns what his brother likes or responds to. Sam bites and sucks at Dean's neck. He tries to forget about Ruby, about demon blood, about Ellen and Jo and how Castiel is now screwed too... He learns the taste and feel of Dean's skin and when he can feel an answering hardness, Sam feels a dual flush of heat and guilt. Dean's words only cause his own dick to harden, thriving on the praise. 

And then Sam is pulling away and yanking his t-shirt off. He's scrambling at Dean's shirt next, not waiting for permission as he rips it off of Dean. Both shirts lie on the floor, forgotten. The room is bright with moonlight streaming through curtains and Sam is glancing down at his brother, taking in the now-exposed torso. 

He wants to say 'see? I'm bad for you,' but what comes out is, "You're perfect." Sam leans down, kissing along Dean's collarbones. "You've been everything to me," Sam begins, kissing at Dean's chest. "A dad. A mom. Brother. Best friend..." 

His tongue flicks out to tease at a nipple, curious if Dean will like it.

* * *

This is wrong, but Dean isn't protesting. He'd lost the right to protest the moment Sam had kissed him and he hadn't drawn away. Like this, with Sam's lips tasting and teasing, Dean doesn't draw away. He wants to remember this. He wants to remember every part of this for later, if he has a later without Sam in his life. He watches as Sam draws back, and while Dean's mind doesn't catch up with all the naked skin revealed to him until Sam is already tugging at his shirt, he gets the hint eventually and shifts, helping Sam strip his torso down to toss the shirt aside.

Dean looks. Though the moonlight doesn't illuminate much, he can see enough of Sam's body to lock everything home. The anti-possession tattoo on his chest almost makes Dean want to laugh hysterically given what they're about to do, but the rest is enough to catch his attention. Dean looks his fill as much as he can before Sam is suddenly speaking, and the words feel like hot coals raking over his skin. Dean shuts his eyes, his lips thinning. 

He's not perfect. No perfect brother would let his own blood jump into the pit, but he tries to just focus on the press of lips, on each kiss, but Sam doesn't stop. 

Dean's hands move up, wandering over the broad, powerful expanse of Sam's back. His fingers catch on small, faded scars, and he names them in his mind. Shifter in Minneapolis, ghost in Seattle, poltergeist in Kansas. Knife, knife, claws, teeth, and all faded so much that in the light of day, they look almost normal. Dean traces a slightly bumpy line on Sam's side that he remembers stitching up himself and he closes his eyes to lock it all away. It's easier than focusing on what Sam is saying, because if Dean lets himself think about any of this, he's sure he'll fall apart.

"Sam," Dean says, and he sounds almost desperate for Sam to _not_ tell him what he'll be losing. He can't. 

So instead Dean lets himself fall into the sensation. He's only had a few women pay his nipples any attention, so the first touch to one leaves him grimacing at the weird sensation. It takes him a second to decide if he likes it. His cock is what eventually tells him that yes, yes he does, and Dean bites back a curse as he reaches one hand up and curls it tight in Sam's hair. Finally a use for it. Dean grabs him closer and holds him there and despite the grief, despite everything, the fact that Sam can push and fight his hold is hot. Dean arches up against him, and his free hand works between them to skirt over the powerful line of Sam's chest. 

"That's okay. That's... fuck, Sammy, that's good." It's easier to praise than to acknowledge the rest.

* * *

Sam still remembers feeling a sense of excited hope at the prospect of angels existing. An angel of the Lord had saved Dean from Hell -- finally something good out there... And then he'd witnessed Pamela's eyes being burnt out by Castiel and he'd met Uriel and Zachariah and most of the angels turned out to be - in Dean's words - dicks. They'd been shuffled around like pawns, they'd got Dean to torture Alastair and they'd pulled Adam into all this bullshit too. But at the top of the dick-angels list is definitely Lucifer and Michael. And Sam knows Dean is just wrecked enough about this to be allowing him to get away with it. Because this is essentially his last night on Earth and he's requested his last meal be Dean. He knows if they weren't in this situation, Dean would be flipping out over this. Even though Sam's pretty sure his older brother isn't exactly as straight as an arrow, masculinity and appearances are important to Dean. Sam remembers how hard John had been on Dean and now Dean tries to maintain that tough image of holding it together, of chasing chicks and drinking beer. He shouldn't be exploiting this, be dredging this up out of Dean-- And yet Sam doesn't stop. Selfish, freak, messed up -- the words shriek in his head, but Dean's tight grip in his hair is nice. It's not quite rough enough to distract him, but it's something. Sam is fairly certain he could overpower Dean, but he lets his brother hold him close and touch him. Dean pushes into him and the praise fills him with heat and anguish. Heat, because Dean sounds hot and he wants to make Dean feel good and anguish because he's not an idiot, Sam knows this isn't good for either of them. But he licks at Dean's nipple, he lets his teeth catch it and he tugs on the pebbled hardness just to see Dean's reaction. Dean is all heat and hardness, rough hands, so different than the women he's taken to bed, but so similar to himself. The realization hits Sam hard and he suddenly pulls away to allow himself some space. 

"Going to make you feel so good, Dean," Sam murmurs lowly in-between kissing down Dean's torso and a smooth stomach. "Just let me, all right?" He glances up as his hands come to the button on Dean's jeans. Sam leans back. He may be a freak, but permission is still important.

* * *

It's a rare occasion that sees Dean dropping his humor by the wayside, but considering how his world is about to end, he thinks he can be excused. It's so fucking selfish, but sometimes Dean thinks the only thing keeping him going is his brother, which is just awful. Bobby's like a father to him, and _Cas_... Cas has given everything for him, and yet if it came down to a choice... Dean doesn't want to ever have to make that choice. Not because he can't, but because he _knows_ what he'd pick and he hates himself for it.

So he drops his humor and lets himself feel. Sam's touch feels good even if this whole goddamned situation isn't. If this is what Sam needs, Dean's not a big enough man to stop him. He doesn't want to. It doesn't matter that he's never done this with a guy before; Sam's owned him - his mind, his heart, his loyalty, his _life_ \- since they were young. Why shouldn't Sam complete the set? Why shouldn't Sam have his body too? Dean isn't sure if he'll be using it for much longer without Sam in his life. Time beyond 24 hours seems empty and bleak and so he makes this count. 

He grinds out a rough curse when Sam's mouth comes down hot over a nipple, and he tugs Sam's hair at that first scrape of teeth. It's new but it feels good. All of this feels good physically, at least until Sam suddenly draws back. Dean _almost_ asks him what's wrong before he catches himself. A part of him wants to laugh hysterically and ask what _isn't_ wrong but he doesn't. Instead he clings to Sam's words and arches into the kisses. 

And when Sam asks permission, Dean's eyes close with a shudder and he tells Sam what he'd never told Michael: "Yes, fuck yes."

Dean's dick is a hard line in his jeans, tenting the fabric as much as denim will allow. His chest moves with every breath and Dean takes only a moment to center himself before he opens his eyes again and looks down at Sam. It's not a sight he's used to seeing. It's weird. It's wrong. Dean's distantly aware that Cas and Bobby aren't too far away from them, but he can't bring himself to care. What does it matter? What does anything matter? If this is what Sam wants, then it's all Dean can do to avoid yanking his jeans off by himself. Instead he props himself up on one elbow just so he can reach down and touch Sam's face, the line of his jaw, the swell of his cheek. Dean hardly ever touches him unless he's injured, and he suddenly hates himself for it. So much wasted time. He won't waste this. 

"You let me make you feel good, too. I got you, okay?"

* * *

He's granted permission. Dean tells him _yes_. Sam's going further - falling further - crossing lines that shouldn't be crossed, but he's not going to have to live with the fallout. He's a coward but Dean… of course Dean will have to bear this burden. Dean will have to deal with this new mess he's creating. Sam just hopes Lisa and Ben can pick up the pieces, that they can hold Dean together because Sam's going to be occupied in the cage with a couple of pissed off brothers.

Dean looks down at him and although his brother is aroused, Sam can fucking see those _cracks_ that Dean is hoping won't break (or at least won't break in his presence). Dean's always had the notion that showing weakness was to be avoided, so any breakdowns are usually private or when the crap gets piled too high and spills over. Sam wonders how many cracks are from him -- from his doing. How much has he stressed out Dean? Tested him? Lied to him?

Sam forces his fingers to move, unclasping the button and dragging down the zipper. He's got to keep things moving. He's got to at least blow Dean's mind in this one thing. But then Dean's hand reaches out and touches his face. The touch is _sweet_ and it hurts; Sam quickly glances down to hide his wince, his hair falling into his face to shield his expression. He doesn't deserve sweet and comforting, not when he's corrupting Dean in this. 

Dean's damn words then filter through. ' _You let me make you feel good, too. I got you, okay?'_

"Yeah, 'course," Sam agrees breathlessly and then gets to it. 

He works Dean's jeans off first and then the boxers are stripped off. His hands shake a little, but Sam is on a mission here as the clothes pile on the floor increases. Dean is exposed now, completely naked to him and Sam feels a sick thrill at being the one to bring this about. They've always been close, but now this is a step _closer._ (There's something wicked inside of him that delights in the idea of knowing and having Dean in _every_ _way_. It's a nasty covetous feeling, obviously abnormal, but it's there anyway.) 

Sam settles between Dean's legs, on his knees. He gives Dean a small coy smile as he runs his hands down firm thighs and bends over, opening his mouth and with no further fanfare takes the head of his brother's cock inside his mouth, sucking softly. It's been years since Sam has done this, but he knows what he likes. There's a bit of nerves (new sexual partner, gender he's not normally into, an activity he's not really comfortable with) but Sam is nothing if not tenacious and determined.

* * *

With every second of this, Dean wonders when his common sense is going to kick back in. He watches as Sam undoes his jeans, the belt buckle heavy enough to hit his thigh when it's undone. He doesn't protest. Dean watches as Sam's fingers (a little softer than his own, a little longer) undo the clasp and zipper of his jeans, and still he doesn't protest. Instead he lifts his hips when he's prompted to and he feels the worn denim slide down over his legs. The air in the room isn't exactly cold, but Deans shivers anyway because with each moment, he knows for a fact that he's not going to be stopping Sam. He lifts his hips again to help Sam work his boxers down, and Dean allows himself a soft breath when his cock twitches in the open air, thick and flushed, and it's a fucking miracle. Not because it's Sam, but because Dean's got so much grief swirling around within that he wonders how he's even hard now.

Maybe it's the thrill. Maybe it's the taboo. Or maybe it's because he needs this as much as Sam does. Though he's not into comparing, he wonders if he doesn't need this _more_ than Sam does, and isn't that a terrifying thought. Wetting his lips, Dean watches as Sam's hands (so fucking big; he's not used to masculine hands on his skin) slide down his thighs, almost as if testing the muscle. Sam's coy smile strikes him and Dean locks it away. He'll remember it. Fuck, he'll remember as much of this as he can. It's not the first time he's been naked in front of Sam, but it's been a good few years. (Sam can't say the same as Dean had delighted in stepping on his towel coming out of the shower a few times. Sam's instant squawking had been pleasing during their pranks.)

He thinks - at most - that Sam might touch him. The thought is enough to send heat through him. But when Sam instead _leans down_ , Dean's eyes widen almost comically before Sam's lips close, warm and wet, over the head of his cock. The sensation is sudden and almost violent; he's not gone home with anyone for weeks. No bar-hopping, no casual sex, no nothing. He's been too in his own head. So this is sensitive for a number of reasons. 

Dean's head falls back on the pillow and he lets out a rough, clipped sound in the back of his throat. It's half-grunt, half-breath, and before he makes the decision to, he's got one hand buried in Sam's hair. Dean's halfway to stroking, encouraging him to take more in before he remembers that Sam's not _done_ this before, and he immediately lightens his touch. 

"Fuck, Sam, sorry. Didn't... didn't think." He still can't believe that Sam is doing this. _How_ is Sam doing this? It's so much all at once but Dean needs it. He spreads his legs a little more so Sam can get closer, and his groan is rough and needy at those soft, almost-tentative little sucks. Trust Sam to go all in.

* * *

Sam isn't a prude. He's never seen the point of caring all too much about nudity, but he's never been the type to go parading around either. Dean is more compact than him, but there's a real strength in his smaller (read: more normal sized) frame. Aesthetically, women have always been his go-to, but a bit of college experimentation has taught Sam that he's flexible, that a male hand or mouth on his dick still felt good and that hey, a hole is a hole...

Dean isn't just anyone, though. Yeah, his brother is traditionally good looking, like a dumbass male model type, but Sam's never allowed himself to gawk at him before. They had boundaries. A guy code while on the road. They didn't disturb each other when one of them had a girl (most often Dean, not him). They left if one of them woke up with morning wood to take care of. They were respectful. Most of the time, anyway unless Dean felt like giving him a rough go of it, but that was to be expected of an older brother and all.

It has to be the sheer gravity of their situation that's getting to him. Desperation flipping some switch because surely he can't be _this_ fucked up, right? Sam tastes Dean in his mouth, the silky tip of his cock against his tongue, hot and hard because of _him_ and Sam wishes it didn't make him so damn excited to be doing this, but his hormones feel like they're in overdrive and Dean pushes him down and yeah, that's hot too, he wants Dean to use him, to fuck his mouth and feel good--

The apology catches him off guard, enough to pull away. Sam chuckles a bit, glancing up at Dean. "It's all right, it's not my first time. You aren't going to scare me off," he reassures. "Watch me, though... Watch me, Dean." 

The lighthearted tone is gone from his voice as he shuffles down, the tips of his finger pushing Dean's cock toward his belly, allowing Sam to lick the underside from the base to the top. He repeats the motion, breathing through his nostrils as his tongue learns the feel of his brother in this new intimate way. Sam doesn't plan on teasing though, so after a third lick, his mouth opens wide again and he moves down on Dean's dick, sucking hard and pushing himself to take more until he feels his throat start to protest. 

* * *

Dean's apology makes sense to him. _He's_ never gone down on a guy before and so he just assumes Sam can make the same claim. So when Sam draws back just enough to look up at him and then chuckles, Dean blinks dazedly down at him, his brow furrowing in breathless confusion. Laughter isn't really something he's expecting like this, but despite his confusion, it makes him feel good. It feels like it's been an eternity since he's heard Sam laugh, and Dean feels the twist in his heart the second before Sam's words absolutely short out his mind. 

It's not Sam's first time. It takes a few moments for those words to work their way past everything else, but once they do, Dean's eyes widen in shock. 

"You-- wait, what-?" He begins to talk, tries to, anyway, but then Sam cuts him off with a low request for Dean to watch him. The tonal shift is enough to almost give Dean auditory whiplash and he can't fight back his own shiver as he does just that. He doesn't need to be told twice. He looks, the flush to his skin impossible to see in the dark, but the lax, awed expression is clear. 

And when Sam presses Dean's cock down to get a good angle for his next lick, Dean grunts and bites out a curse. He almost takes his hand away from Sam's hair before he remembers he's been given permission and just like that, Dean slides his fingers back through Sam's hair. Suddenly its length seems like a great fucking idea.

Sam's tongue feels fucking amazing, wet and hot and catching every place he's sensitive. Maybe this is wrong, maybe it's monumentally fucked up that he's got his little brother's tongue on his dick, but Sam has always been so much more than _just_ his little brother. Dean can't regret this now. He isn't sure he ever will. 

Instead he bites his lip as Sam's mouth opens and the second Dean feels the heat, he hisses a sudden, "fuck, oh fuck, Sam," and his grip in Sam's hair tentatively tightens. 

Suddenly it's not enough. He doesn't even think as he frees one hand and throws it out, groping blindly for the side table. He touches the lamp there and in a rush, he doesn't just see Sam's moonlit silhouette. He sees Sam under the golden glow of the lamp and the sight - the real, visceral sight - of Sam's lips stretched around him is so hot and mesmerizing that it's all he can do to keep his hips still. Dean watches Sam like he can't bear to do anything else. He can't. Sam will be gone soon and this... fucked up as it might be, this is something he'll never forget. Each hard suck draws a moan from Dean's throat, and when the back of Sam's throat squeezes the head of his cock, Dean bites back a shout and his fingers curl tight in Sam's hair. 

"E-easy, Sammy, it's... it's okay. _Fuck_ it's more than okay."

* * *

It's honestly a little endearing that Dean had just _assumed_ that he has zero experience with other guys. Sam supposes that he has never given any indication to prove otherwise. And Sam really _is_ mostly straight, but orientation and preferences don't matter. Not now, not here. Not when he's willingly going to say _yes_ to Lucifer in the hopes of taking back control over his body and then jumping into the cage. (He has to believe that he's strong enough to do it, please God help him be finally do the right thing.) Goodbye world, goodbye Bobby, Cas and...

Dean.

Dean's already been to Hell. For him. Maybe this is his turn now. Some atonement at the very least. Sammy finally being all grown up and cleaning up his own mess. Even so, he doesn't want this. Sam doesn't want to leave everything, to leave Dean, but end of the world Apocalypse crap is a compelling reason. It's the only real shot they have. The only legitimate plan they've had other than attempting to kill Lucifer with the Colt and that had been half-baked at best. If the other angels won't help them, if God is done with them, what other choice do they have?

They don't have other viable options. Sam's made his choice and now he's making another. He's blurring the lines between them, staining Dean with his filth, but need and desperation have their hooks deep within him. Dean's hand slides back into his hair, the grip tightening, the tug sending a shiver through Sam. He both hears and feels Dean going for the lamp. Warm light filters into their shared room. Sam knows the light is on for him. Because he told Dean to watch. To watch _him_. And now Dean is really watching him. More detail, like how hair annoyingly is falling into his face and the moisture collecting at the sides of his mouth. His throat convulses at the unpleasant sensation of having a dick trigger his gag reflex but Sam only backs off a little. It's Dean's reaction - his fingers gripping hard in his hair and the assurance - that makes up for any unpleasantries. 

In this heated moment, it's all about Dean. Dean's cock may not be greater in length than his own, but Sam thinks it's thicker. And the realization shouldn't cause arousal to spike. Sam bobs his head, sucking hard and caressing the underside of Dean's dick when he remembers to. He feels spit begin to accumulate in his mouth and with a shudder Sam eventually pulls away, wiping at his mouth before swallowing the excess saliva.

"Roll over, Dean," Sam then instructs as he sits up and budges over to allow space. He knows what he wants to do and he knows he's damning himself. Well, now he will have another reason to be in Hell.

* * *

The lamp doesn't show him anything he hasn't already seen before. He's seen Sam in various states of undress but there's something _more_ to it this time. He can see the arch of Sam's back, and the way his hair falls down over his face when a few strands escape Dean's hands. He quickly moves to brush them back even though a voice in the back of his mind tells him it would be safer to let Sam's hair hide him. It would be easier to just assume that it's _not_ Sam currently sucking his cock, that it's not Sam he's laying naked under, but Dean doesn't care. He can't. Sam's mouth is what he feels heaven should be, all wet, tight, hot suction that means so much more because it's _Sam_. Dean bites his lip until it hurts, his breath coming out in quick puffs of air as Sam works him.

Dean just watches, transfixed, as Sam sucks him, his lips stretched around Dean's cock, the golden lamplight reflecting off of his hair and his cheekbones. The picture he makes is perfect and it's all Dean can do to keep his hips still, to _not_ thrust up into Sam's mouth. He feels the soft inside of his cheeks, feels Sam's tongue working over him, and Dean's groan is almost too audible as he grips and strokes at Sam's hair. 

But when Sam draws back with a sinful wet sound and swallows, Dean just looks at him, dazed, and though he's got no fucking idea what to expect (well... okay, no, he's got _some_ ) he only hesitates for a second before nodding. His dick twitches unhappily at being abandoned, and he untangles his fingers from Sam's hair to give himself a quick stroke to calm himself back down. Then Dean leans his weight to one side and gets up onto his elbow, then promptly turns over onto his stomach. He's not sure if Sam wants him on his knees or not, so for now he just lays there. Instead of pressing his face into the pillow, though, Dean reaches down to adjust himself and then looks back over his shoulder at Sam, breathing hard still, a question in his eyes. 

"You just... however you want me, man. Just say so."

* * *

Sam feels a jittery sort of excitement, nerves and arousal warring, but the latter definitely is more dominant. He remembers thinking that it all was too much for Dean (or any man) to handle... Being a servant of Heaven, God apparently having some big plan for him. Turned out the angels had their own plan and a stupid one at that. Sam tries to not think how disappointed he really is at the supposed good guys actually not being so good. (Just _once_ in their lives it would have been nice, okay?)

Dean listens to him, not even a question thrown his way as he obeys. It shouldn't cause Sam to be _more_ turned on, but it does. It really does. His older brother bending to him? Exposing himself in another way? Trusting him? 

But it's it trust, or is it simply Dean beaten down into submission? The ragged remains of his brother rolling onto his stomach... Even if that is the case, Sam's erection and arousal don't flag. Maybe now more than ever Sam realizes that a part of him _does_ belong in the cage with Lucifer and Michael. He's got to be taking advantage of Dean's grief here. That's the only way Dean would be allowing this. 

It doesn't matter. Dean settles on his front and then gives him the wheel, so to speak. Sam swallows again, he's on his knees by Dean's waist as he looks over the expanse of Dean's toned back. There's a few scars. They both have 'em. He knows this body laying before him, but he's never known it this well. Sam lets his hands come to rest on Dean's shoulder blades as he squeezes the muscle there in reassurance. 

"Spread your legs for me," he says, voice steadier than he feels. Dean complies and as Sam comes to crawl in between Dean's legs, he rubs along Dean's back, up and down, enjoying the strength and warmth found there, and then lower, above Dean's ass. 

"This will probably feel strange, but just let me try." Sam's palms brush over Dean's ass and he gently kneads the skin there, hoping to relax his brother. "I'm going to lick you, all right?" He spreads Dean's cheeks open, a tight hole waiting for him. Sam's fairly certain Dean's never been this adventurous with girls before to be on the receiving end, but Sam has once and he knows it's going to drive Dean wild if he lets himself go.

* * *

Would Dean be doing this if it wasn't life or death? Probably not. But that doesn't mean that he doesn't want this. On some level, if he truly didn't want to do it, he'd say so. He'd push back. But he doesn't because there's a part of him that does want this. He wants the shock of the memory, and even though it's going to kill him later, every time he has someone go down on him, or touch him a certain way, or kiss him, he wants to think of Sam. Soon all he'll have are memories and Dean has no idea what he'll do when he has nothing left. Hopefully this will help as much as it can. 

So when Sam tells him to roll over, he does. When Sam's hands touch the skin of his back, Dean slowly begins to let himself relax, and when Sam tells him to spread his legs, Dean swallows back a small thread of nerves and does what he's told to do. He slowly spreads his legs, wiggling a little to get the job done despite so little space on the bed. He thinks he knows where this is going, and while he's nervous, he lets himself relax. There's a small part of him that wants to protest that he's the _older_ brother, but it dies quick enough; Sam knows what he's doing, and this... this will be a visceral sensation and Dean wants it, even if it will hurt.

He feels the bed dip as Sam shuffles between his thighs and he lets himself relax into the small massage. He tenses just for a second when Sam's hands drift down, but he quickly reminds himself that this is _Sam_ and his protests disappear. Dean shivers instead and nods. There's nothing in him that thinks Sam is going to do anything else aside from fucking him. The positioning is right, and Dean's already considering pointing out the lube in his duffel bag when Sam's hands drift down to his ass and Dean's breath catches. 

He grinds out a rough, "wow, fuck," because aside from women gripping his ass when they're about to come, people don't touch him there often. It's Pavlovian when they do; someone touches his ass, it means he's doing a good job. So his dick twitches against the sheets and Dean lets his brother massage the skin, relaxing more as time goes on.

But when Sam chimes in and says he wants to _lick_ him, Dean's mind blanks. Initially it's in confusion (Sam _had_ been licking him; rolling him over seems to make licking him harder) but as Dean's mind sluggishly connects the dots, it dawns on him. Admittedly he doesn't understand until Sam is spreading his cheeks, and then a deep flush steals across Dean's skin at the knowledge of what Sam wants to do. 

"You-- Sam, that's not--" Dean cranes his neck back as much as he can, and he really is all set to protest when he makes the mistake of looking at how earnest Sam's expression is. Dean's protest dies in his throat and when he swallows, it's both nerves fueling it as well as uncertain approval. "If... fuck, if you want? This is Greek to me, man."

* * *

Sam knows this is wrong. He's not always an idjit as Bobby would say. He knows that 'keep it in the family' has limitations. You keep the family business under wraps, you only share when absolutely necessary... And no matter how dire the situation is, you don't go jump your older brother. Christ, he doesn't even want to know what their father would say if he knew about this now, let alone those who are still living (Bobby, Cas)... Sam's certain it wouldn't go over well because this kind of shit _isn't_ supposed to happen. Dean would never do this in a million years. But he's Dean's pressure point, he makes Dean weak and right now he's exploiting that.

So Sam may announce his intentions and it may look like he's trying to be considerate, but he knows Dean is going to let him do anything tonight. He's going to get away with everything tonight. Dean isn't going to lock him in the safe room and tie him down. Dean is going to let him say yes to Lucifer and Dean is going to say yes to him because of it. It's the guilt, Sam thinks. It's the fucking guilt that Dean tries to drown with booze but is never successful doing so.

And it may start as some feeble embarrassed protest, but when Dean looks over his shoulder and sees his expression, something changes. Dean's guilt and grief help Sam here, they're good co-conspirators in this. And Sam _does_ feel bad about doing this, but he'd rather feel bad than scared. He's used to feeling bad, he's used to being the freak. This just solidifies it. Arousal and desire and desperation have him steady as a flicker of a smile shows up on his face. 

"Keep an open mind," is all Sam says before hunching down and getting onto his stomach. He spreads Dean open again before taking a deep breath and moving in.

Sam doesn't necessarily enjoy having his face in anyone's ass, but he enjoys shocking and surprising his partners by doing something supposedly dirty. He enjoys the squirming and expressions of sensitive pleasure. He likes working them up, getting them to beg. Sam doesn't hesitate with Dean. His tongue pokes out to lick hotly over the exposed hole. They're broad licks, light, but enough to introduce Dean to the sensation. He keeps the pace steady as he slowly laps at the tight ring of muscle, curious to how Dean will react.

* * *

Dean's never done this before. It goes beyond never having this done to him and straight out to never having done it to anyone else, period. There have been a few accidents in the past, sure. Dean likes going down on women when the mood suits him, and while he's usually content to lay between their thighs and go to town like that, there are times where he likes to get them onto their hands and knees and eat them out from behind. There have been times he's licked too long and his tongue has glanced over the ass but that doesn't mean he'd focused his attention there. If anything it had almost weirded him out at the time, so that Sam actually wants to do this to him is almost unthinkable.

Almost. Dean feels the shiver of desire climb through him as he gives Sam the go ahead and the bed dips again. Dean looks back and just barely manages to see Sam lay down on his stomach. Dean's mind blanks helpfully for a second and he swallows because he's not sure what to expect, but he does want this. He shivers, feeling each of Sam's hot breaths against his skin, and he knows he's not going to forget this. This isn't going to be something he experiences and dismisses later. It's weird, it's more adventurous than Dean is used to, but that doesn't make it bad. Instead a hot flush crawls through him and when Sam's hands spread him a little wider, Dean's lower lip slides between his teeth.

The first pointed lick doesn't feel like much aside from a bit of a shock to Dean's system. It's an unfamiliar sensation and it curls through him sharp and sudden, but it's over before he can decide whether or not he likes it. Dean's breath draws in sharp and he shifts, squirming a little, but it's not until the second touch of Sam's tongue that sensation really creeps up on him. The next lick is slower, broader, and Dean makes a small sound, sudden and almost startled at the feeling. It's wetness that he's not used to, but more than that, it's sensitive. He's not really sure how that can be sensitive but it is. Yeah, he's let women use a finger here and there when they're into it, but this feels different, feels sharper. Dean's breath escapes him on a punched-out sound and tension creeps into his shoulders as he grips at the sheets.

It takes Dean until one of the first real licks for the sensation to translate into something that feels good. His breathing catches and he grinds out a soft, breathless curse, his dick twitching against the bed, trapped between the sheets and his stomach. 

"Fuck, that's... Christ, Sam," Dean breathes shakily, and his legs spread a little more without his say so. "Mind is open. Feels... Feels good, man."

* * *

This isn't how Sam thought he'd be spending his last night. He should probably be trying to get a good night's rest (they both need it), but hey, when's he ever made the right decisions? For as many miles as they've traveled, there exists an equally long list of his mistakes trailing him. And through it all, Dean hasn't given up on him. Even after the Ruby fiasco and even after he'd helped free freakin' Lucifer, Dean hadn't abandoned him. Sure, they'd gone on their own for a bit, but it hadn't _lasted_. That's what mattered. They're here together. 

And he's on Dean's bed. He's kissed him and stripped his brother naked. He's given Dean head and now this. _Rimming_. He's spreading Dean's asscheeks apart and licking him. Sam doesn't lose himself in this -- he could, it would be all too easy to let loose and go for it. Instead, he tries his best to pay attention to Dean's responses, the fidgeting and sharper inhales. He's not that messed up -- he doesn't want this to be bad for his brother. That's the last thing Sam wants. Sam wants to make Dean feel really good. Sam wants to distract Dean -- distract himself, really. One last night as himself, one last night to be alive and human.

He hears Dean react and Sam is pretty sure it's a good sound, so he persists. He licks softly, but not to tease. He wants to let Dean adjust to the sensation gradually and not rush, but it's difficult. Now that's he's really doing this, Sam wants to go further, he wants to get Dean nice and loud and worked up. He wants to push his tongue inside Dean and know him more intimately. 

Dean's comment has Sam feeling a rush of satisfaction and he stops to give a huff of a laugh. "Hey, I may be younger but I know things." Joking is good, right? Sam doesn't hesitate before returning to the task at hand. He licks with more fervor, lapping against Dean's hole with broad even strokes. When he thinks Dean can handle it, Sam uses the tip of his tongue to then flick against it. He can feel the bottom half of his face start to grow wet from his own spit but Sam doesn't mind. He's committed to this. Good sex usually isn't pretty or dignified anyway. 

* * *

This isn't something that Dean could have predicted. Things like this don't happen to him, except when they apparently do. His breathing feels caught in his throat, packed in so tight that the tension radiates to his shoulders. Dean has no experience here. He doesn't know how he's supposed to react to this. It's not like he's looked up porn of this specifically, and even then, porn isn't really a great way to predict how someone's going to react. All Dean's got is genuine reactions, but maybe that's all he needs. He's a little stunned as he pants, his legs spread, Sam laying between them and still licking at his ass. He'd never expected this. Not from Sam. Not from anyone.

It's fitting that this is _Sam_ though. Dean feels every lick, feels the steadiness, the slight prickle of stubble on his brother's jaw. He feels the wetness, hears every sound, and _fuck_ if it isn't both hot and embarrassing. Had anyone told him even a week ago that getting eaten out would feel so good, he'd have grimaced and/or punched them in the face. Now Dean can only squirm, breathless, aroused, closing his eyes as he grips at the sheets and Sam's tongue licks steadily over his skin. 

Dean tries to stay still, tries not to squirm like a little bitch, but it's hard not to, especially when Sam ups the ante. Each lick feels like it's got a direct path to his cock, but it's different, sensitive, and he finds himself shaking as Sam speeds up. He downright moans when Sam's tongue points a little and presses in just a bit. It's _way_ weird, but the way Dean curses breathlessly and his hips ease back just a little says a lot.

"Fuck, Sam," Dean grinds out, and somehow saying Sam's name like this makes him feel even more like a deviant. Arousal twists sharp through him, and there's no way he's forgetting this. He feels broken open in a sense, dejected by the realization that Sam won't be here tomorrow, but it means he needs to chase these memories. He bites at his lip hard and wars with himself for a few seconds before giving in. Dean pushes back, chasing the sensation, and he groans breathlessly. Sam's holding back. Dean can feel the tension in his hands. "C-c'mon, man," he urges, breathless. "It's okay."

* * *

Sam actually hasn't done _this_ before. He's had it done _to_ him and it had been a wild ride of strange intense sensation -- not something he'd want all the time, but definitely something he'd not say no to. College had been a good time for him. He'd felt close to fitting in, at least closer than when he'd been dragged around on hunts with their dad, always the new kid, always the stranger. Sure, Dean had made it bearable, but Dean had suffered in his own way. Dean had been dad's obedient little soldier, forced to grow up far too quickly. Hell, Dean had practically raised him. Sam sometimes wonders if Dean has ever begrudged him his existence. Complicating Dean's life since he popped up...

 

At least at Stanford he hadn't been considered a freak. Experimenting was normal. _He_ was normal, or close enough to it. He also hadn't been weird because he actually _liked_ school and got good grades. But that life hadn't been for him. Perhaps in some other universe because ever since 'ole Yellow Eyes had dripped demon blood into his mouth, he was a goner. A lost cause. But he's going to do some good. He'll fix this up. He can do that much.

He'll also blow Dean's mind. He'll be a freak here is it means making Dean feel really good and distract him enough from this shitty situation that sounds impossible but isn't. Talking had never been their thing anyway. _Doing_ , though? Powering through? Yep. Winchesters through and through. Dean's voice - hearing his name in that breathless way - it's beyond hot. God, he'd heard Dean with more than a few chicks while growing up, and pressed against the door, his jeans growing tighter, he'd known there was something fundamentally wrong with him. 

Sam had purposefully never thought about it. Tried to focus on the females... But Dean pushes against his tongue and Sam has to grind into the mattress to give his own straining dick some relief. Even now Dean knows him, knows that he's trying to go slower than he wants -- to be accommodating. But Dean gives him permission to go further and that Dean trusts him in this... (His chest feels tight.)

Sam doesn't make Dean wait or ask again. He pointedly pushes the tip of his tongue against Dean's hole and works it ruthlessly, pushing in just a little and then retreating. It barely mimics fucking but just the insinuation is enough to have Sam grip a little tighter and moan.

* * *

Dean knows Sam is holding back, but that doesn't mean he's ready for the way Sam just snaps into motion. This is what Sam has always done, surge into action at the drop of a hat, and in a way Dean almost wants to laugh (or maybe cry) because that's just so _Sam_ that it's not funny. It makes sense that Sam's like this in the bedroom too. Dean's not the best at planning. He acts on impulse and instinct, but he tends to have a pretty good compass in his noggin'. 

Sam... doesn't, but Dean can't fault him that now. Not with what's looming over them. So while Sam immediately presses in closer and those slow licks turn into something tensed and pointed, Dean reminds himself that - once again - he's followed his instinct and looked before leaping. His only consolation is that Sammy is right there with him.

And in a way, Sammy is right there _in_ him. Dean feels the flex of Sam's tongue (a weird-as-fuck sensation) and if anyone asks him how this feels later, Dean's not entirely sure he'll be able to figure it out. It's just... _more_. More heat, more closeness, more touch, more breath and saliva against his skin. He feels wet, which isn't a feeling he's used to, but before he can really start to care, Sam's tongue fucks into him and Dean's body seizes in a sudden twitch. He only belatedly manages to bury his groan in the pillow under him. Bobby and Cas are in the room over, but there's a small side of Dean that just doesn't care. Let them hear. He doesn't want to be censoring himself tonight. Not when this is all he'll ever have.

It's that thought that makes Dean shift enough that his forehead presses against the pillow. It leaves a warm hollow between his chest and the mattress for him to breathe, and while his voice is muffled and the air is stuffy, it means Sam can hear him. 

"Fuck, _fuck_ , Sammy," Dean manages, rough. He has no muscle memory for this and so his body just shakes, trembling slightly with the mix of sensitivity. When a chick goes down on him, his hips know to jerk up (if she's cool with it) but he's got no frame of reference for _this_. So he's almost relieved (and really fucking embarrassed) when Sam groans all hot and rough against his ass and the vibration sends sensation flooding him.

Dean's gasp is like a physical thing and he presses back, chasing the feeling without thinking. "God, what-- a-again, man," Dean breathes, hands clutching at the sheets. "Do that again."

* * *

Sam may feel a familiar frenzied urge coursing through him (a hunger), but this is nothing like his times with Ruby. Yeah, it's messed up, but it's a significantly _different_ _kind_ of messed up. When he'd succumbed to Ruby, he'd been alone and desperate. It was rough and violent - feral almost - and his heart hadn't been in it at all. It had been a means to an end. With Dean gone - Dean in _Hell_ because of him - becoming strong enough to kill Lilith had dominated everything. It hadn't mattered that he'd sunk low enough to drink demon blood and even screw one.

But this thing - this gnawing ache - it's been with him for _years_ it feels like. It took hold of him when he was young, when he first felt irrationally jealous at Dean blowing him off to spend time with a girl and he hadn't understood why it bothered him so much. It burrowed in deep when he'd pretended to be asleep when Dean had occasionally jacked off in their shared hotel rooms. Sam liked girls still. He'd had girlfriends. He'd been planning on marrying Jessica even, but there had always been a selfish part that wanted Dean to be kept all to himself. Best friend. Big brother. Parent. Dean is his everything. Always has been, always will be. 

It's wrong. _He's_ wrong. But they're going to never talk about this. Sam knows they won't be. It may be wrong, a sin - a perversion at the very least - but Dean is so ingrained within him that it doesn't feel wrong in a way that feels _bad_. They're beyond co-dependent. Zachariah hadn't been lying and he doesn't freaking care that for once an angel was right. All Sam cares about is how Dean shakes and the muffled sound of pleasure that's given. Dean shifts enough to move his mouth away from the pillow and the cursing and ' _Sammy_ ' makes Sam flush hot with pleased arousal. 

How long has he wanted this very thing? Too long. His tongue doesn't relent. It honestly takes Sam a moment to realize what Dean is asking for. He's not exactly practiced at this particular activity, but he clues in that Dean must like _him_ being vocal. So, Sam groans again. His tongue spears in and out and it's wet and hot and _perfect_ (in a way that terrifies him). Gradually he notices Dean's hole relax against his tongue and Sam isn't quiet. It twitches against him, receptive and sensitive, but the initial resistance eases and only then does Sam finally pull away, wiping at his lower face with the back of his wrist as he gets up to his knees.

"Want to fuck you, Dean," Sam says, voice tight. The words _finally_ vocalized cause Sam's stomach to jolt in a sick anticipation. He lets his index finger slide in between Dean's slick cheeks to run down over his hole in a light tease. "Can I?" They both have lube. That's the next step, but permission comes first.

* * *

There's an itch under Dean's skin, low and intense, burning and hot that he can't really scratch, or that's what it feels like. Every time Sam's tongue presses in close and slides just that little bit _in_ , Dean's body twitches and he can't help but _want_. He's not even sure what he wants, just that there's desire and longing and he wants everything. His cock is hard and leaking where it presses up against the bed, but Dean doesn't rock down to grind against the sheets. Instead he rocks back, chasing that building itch from Sam's tongue, his breaths steadily going from even to punched-out and shaking. Dean's hands rhythmically clench in the sheets, muscles taut in his shoulders, but the more Sam works, the more Dean's mind zeroes in on that, on Sam.

He still knows what's coming tomorrow. He still knows what he's going to lose. He can't forget that, it's so deeply ingrained in his heart that if he lets himself focus on it, he feels like he's dying. So he focuses on Sam instead, on the wet fucking of his tongue, on the way Sam keeps him spread, on each low groan Dean had only heard a few times when they'd been younger. Each one sends sensation curling through his spine, his breath hitching, and Dean doesn't even realize how into it he is until suddenly Sam's hands relax and he moves away. Dean presses back just a bit before he clues in, and he pointedly doesn't think about how much of a bitch this makes _him_. Instead he shakily shifts, resting his cheek on his pillow, breathing heavily for the few seconds before Sam talks and tells him what _else_ he intends.

It's a desire, a question, but it may as well be a command for all Dean has the heart to deny his little brother anything at this point. His dick is hard, his skin damp with sweat, and he can feel that itch curling through him. The tightness and the ache in his cock is one thing. He gets that. The itch for _more_ is new, and as Dean shakily swallows and lets himself picture just what he's signing himself up for, he wonders if Sam is trying to ruin him for anyone else. Dean honestly doesn't mind. 

"Yeah," he breathes, his voice shaky as Sam's finger trails back down. He's beginning to worry that the itch he's feeling is like a woman's desire to get fucked. Trust Sam to shake things up like this. 

"Yeah, Sammy. You want to fuck me, you can fuck me. Just... just tell me you know what you're doin'. And stop being a damn cocktease," Dean adds, trying and failing in his attempt to _not_ press back against Sam's finger.

* * *

There's no turning back now. He's gone too far, but Sam's already said the words. He's asked for permission. Having sex with Dean. Fucking his big brother? Sam shouldn't want to, but he's wanted it for years now. He's twenty-seven and ever since he was a teenager he's been just a little too in love with his brother. A little too interested in him. A little too bothered. A little too angry about their Dad pushing Dean. _He'd_ pushed it down of course. Sam had done the tried and true Winchester repression. Pushing through and keeping the ugly to yourself. 

But is this ugly? Aren't family and love and devotion good, pure things? Well, good before it involved _him_ because Sam's surely tainted it by now. Dean is good. Dean always has been. Looking after him, saving him time and time again, selfless and soldering on to do good and help people no matter how dire things got. Sam can't help but gravitate toward him. Maybe it's the demon blood, maybe it got his wires crossed as a baby. Faulty programming setting him apart, Sam Winchester, always a little off and needing his older brother to either save him or kill him. Christ, their family was a piece of work.

He's about to make it more of one, too. Dean _agrees_ and Sam would like to say he's a bit shocked, but he isn't. Not really. Dean is wrapped around his finger, chained to him, but soon... After this, Dean can have his normal _good_ life. Free from him, free from his darkness. 

But not yet. Sam exhales a little too loudly when he feels Dean push against his finger. He could probably get the tip in without lube, but he's not going to risk it. He gives Dean's hole a circular rub a few times before pulling away. 

"Yeah, I know what I'm doing," Sam huffs out, a little endeared as he climbs off the bed. He takes one last look at the appealing picture Dean makes spread out on the bed and _willing_. "And this isn't me being a cocktease at all, jerk." Sam goes to the attached bathroom to grab a towel and then pull out lube from his bag. 

"Roll over. Wanna see you," is what he says when he's at the foot of the bed.

* * *

Dean's never been the kind of man who deals with his shit well. When crap gets to be too much and the walls start closing in on him, Dean finds his answer between a pair of shapely legs, on the end of bloodied knuckles, or in the bottom of a bottle. He's never been in this situation before, though. Sex usually distracts him from his problems, draws him away from them so he doesn't have to think about them. He's never had sex with the _source_ of his problems. Not even Cassie, not even Anna; those had been distractions. 

But Sam... Dean aches at the thought of what's going to happen tomorrow, which makes him more desperate to forget, so he throws himself deeper into this which only reminds him of how he won't have this tomorrow, won't have _Sam_ , and it feels like an endless cycle. He should stop, should put his foot down or jerk away and mutter some excuse. Instead, it's Dean that almost panics when Sam suddenly draws back. 

For a horrible, gut-wrenching moment, he thinks Sam's had a change of heart, so when he hears Sam let out that soft huff of laughter and hears his reassurance, Dean lets himself sag against the bed. 

Dean's quick to save face, his body still wired, his muscles still twitching with the stimulation, and just for a fraction of a second, it's like everything is okay. Sam tells him he knows what he's doing and Dean grunts, letting his cheek rest on the bed, just shy of disgruntled. 

"Dude, like fuck if I know what you've done. Playin' it safe here," he mutters, his usual sarcasm, and if he closes his eyes and concentrates, he can almost pretend that tomorrow isn't going to happen. For three blissful seconds, he manages. Then the reality settles on him again and Dean's next swallow clicks dryly in his throat. Sam only leaves for a few seconds, but Dean's pulse is quicker when he comes back. 

A million things curl through his mind like smoke. What is he doing? What is he _going_ to do? How's he going to function without his brother? Isn't there another way? Why is it always _them--_

Then Sam tells him to roll over and Dean's pulse skips again. He looks back over his shoulder for one moment and does what he can to get a grip. This is Sam's last night. Dean's not going to ruin it because he's too weak to man up and lock it all away. He gives himself a moment to breathe and then he props himself up on one elbow. Still shaky, his cock still hard and jutting up against his stomach, Dean shifts so he can roll over and then lays back down on the bed. Sam's still standing, still looking at him, and Dean's more exposed than he's ever been but it's worth it for Sam. Dean swallows. 

"You just gonna stand there, or are you gonna fuck me?"

* * *

It's a cowardly thing to be doing because Sam won't have to face the consequences of this. Dean will have to. Dean will have to live each day knowing how messed up his younger brother really was. Sam's pretty sure he wouldn't have started shit if tomorrow wasn't happening. Sam's held out this long. He's behaved about this one thing (at least). If he wasn't booking a one-way trip to Lucifer's cage, he'd have kept on behaving. He'd inherited the Winchester repression, after all.

Dean's sarcasm is honestly welcome. God, Sam's going to miss it. All the little things about his brother. He thinks he could write a goddamn book about all of Dean's quirks (some of them more annoying than endearing). He's going to miss watching his brother's simple delight in chowing down on a loaded burger. He's going to miss teasing Dean about his Busty Asian Beauties. Sam's going to miss the nights in the Impala with Dean's music softly playing and him dozing off and feeling _safe_. He's going to miss cracking a beer open and watching shit television with Dean. And maybe he'll miss Dean giving him crap too because it's Dean caring about him...

Sam watches Dean turn over, his brother's body practically on display for him in all of its naked glory. It's so familiar: the anti-possession tattoo on Dean's chest, the various scars from claws and scrapes, the look of Dean's shoulders, the slope of his neck-- Sam is pretty much checking Dean out (hey, last chance and all) but then Dean of course has to go give his comment and Sam momentarily feels embarrassed from not moving quickly enough. 

"Yeah, yeah," he mutters, glancing down and clearing his throat. Sam climbs back on the bed. He forgoes slipping his own boxers off. He doesn't want to freak Dean out. Sam may be pretty sure his brother isn't completely straight, but that doesn't mean Dean wants to immediately be faced with his dick. (And Sam is also concerned that Dean may get spooked by the size of _his_ dick in relation to fitting. It is Dean's first time and all.) 

Sam settles between his brother's spread legs and uncaps the lube. He squeezes a fair amount along his index finger. "Tell me if it's too much or if I need to slow down," Sam instructs and with that said his other hand parts Dean once more and he rubs his slick finger against Dean's hole. Sam licks his own lips as he pushes just the tip in. His head shoots up to then catch Dean's expression as his finger creeps into the hot clench of Dean's body. 

* * *

Dean knows he's being a dick, but that kind of programming is hard to completely bypass. He doesn't do well with anyone staring at him, not even Sam. It's not that he doesn't know he's attractive, but it's different with Sam. Dean's afraid that if Sam looks for too long, he'll see how stretched thin Dean really is, how much he'd sell his own fucking soul a thousand times over to keep Sam _here_ with him, or at least to take his place. Dean's been brawling and fighting for scraps his whole life, but not Sam. He's fought tooth and nail so that Sam's never had to. 

He needs to keep it together here, and if Sam keeps looking at him like he's trying to lock every last second of this moment in his mind, Dean's not sure how long he'll be able to just let it happen. He can already feel the plea in the back of his throat and he swallows it down like a bitter pill. But as always he makes sure to keep his expression clear. No regret. No terror. No gut-wrenching brokenness. Just Dean.

Sam's embarrassment still makes Dean feel like an ass but at least it gets the ball rolling. Dean watches as Sam climbs up onto the bed, and there's something about looking up at Sam, _knowing_ what's coming that makes his already-giant brother seem bigger. He's looming, but it's not threatening in the way Dean usually uses the word. If anything, despite his nerves, it's comforting. Sam's still Sam, and Dean locks every second away as Sam settles back between his legs (on the other side this time) and reaches for the lube.

Dean's pulse is quick in his throat as the lube squirts messily out onto Sam's fingers. Dean's only got half a mind to be relieved that Sam's as nervous as he is, and then Sam's warning him, there's a shock of wet cold against his ass, and Dean feels the itch in his gut climb higher and burn hotter. It's different seeing it, seeing Sam's crazy-focus, the way the tendons stand out in his forearm, how broad his shoulders are. The press of Sam's finger is awkward, cold and slick and not at all what Dean is used to, which is why he lets out a soft punch of a breath, eyes almost closing as he squirms.

It's not enough to knock Sam away, but it's also not enough to really make having a finger up his ass comfortable. But Dean, ever drowning himself in bravado, draws in a sharp breath and wets his lips. 

"I can take a finger, Sam. Not the first time I've done it. S'fine, just go for it." Dean fails to mention that he's only ever had a woman's finger up there (he had never been able to figure out the proper angle, and side-stitches aren't great when you're trying to get off) but it doesn't matter. He wants this. He wants to feel it for a long time. (Long after Sam's gone...)

* * *

He's going further and further down the rabbit hole and he's not going to stop. Sam can't stop. Sam needs this. Wants this. And Dean of course is going to give this to him. It should bother him how much Dean would (and has) sacrificed for him. It _should_. It freaking should, but Sam can't be concerned about doing better. It's too late now. It's too late to do well by Dean. If he's to be locked up in Hell, it'll be damn worth it.

Dean's comment has Sam rolling his eyes. Underneath that, he is actually surprised that Dean has had _anything_ up his ass. Must have been an adventurous woman... (Sam isn't sure how he feels about that. In one way it's good that Dean isn't completely inexperienced, on the other hand, Sam is selfish enough that he wishes _every_ first had been with him.) 

"Shut up," Sam grits out and breaks eye contact, looking down. His hair falls in front of his face and he's honestly glad for it right now as it creates a bit of a shield. He feels a little stunned by the sight of his finger inside Dean, at being _allowed_ this. Sam clears his throat before adding on, "That may be the case but you still feel pretty tight to me." 

Sam's finger withdraws before pushing back in, this time with a little less care. Dean feels staggeringly hot and smooth around his finger. Sam's not too concerned about going for his prostate just yet. He wants to get Dean used to this sensation first, so Sam fucks him with his finger. He may not be rough, but he's not slow. Sam knows Dean wouldn't tolerate the delicacy. His own boxers feel tight and uncomfortable. There's a jittery anticipation growing and just knowing what this is building up to has Sam's dick still rock hard. When he feels Dean's body start to relax enough Sam decides that he can move up to two. 

"Deep breath, man," he warns as his middle finger works its way alongside his index finger. He pushes in a little past the second knuckle before withdrawing and then pumping back in. After a few thrusts both fingers are driving in all the way. 

"Gonna fuck you, Dean," Sam blurts out, unable to stay quiet any longer. "Gonna make you feel me nice and deep."

* * *

It's all bravado in the end. Sam's fingers are bigger than anything he's had before, and Dean's nervous, doubt creeping in that he'll actually be able to take anything up the ass. Even if he can't, he'll still do it for Sam, but that doesn't chase his nerves away. It doesn't make him relax around the intrusion. Instead Dean's left breathing a little harder because he swears he can feel every whorl of the pad of Sam's finger as he presses it in. 

It burns a little but it's not a bad feeling, just intense. It's not what he'd call _good_ , but it _is_ close and right now, he wants close. He wants this memory imprinted in his mind in any way he can manage, so he's all set to just deal when Sam speaks up. Dean goes still. There's something about hearing his little brother say: _you still feel pretty tight to me_ that sends something hot and unexpected lancing through him. Dean grunts, tight, and he's suddenly glad that Sam is looking away because he can feel the heat settle quick in his face. 

Dean's bravado does what he'd wanted it to, though. Sam's still careful, but when he pushes his finger back in, it's a little quicker, a little deeper. It's intense, a different kind of would-be-pleasure that leaves him feeling open, vulnerable. Dean bites at his lip as Sam fucks him with his finger. He's not rough, but he doesn't hold much back either, and while the first few seconds are almost too much, the thought of what Sam is doing is enough to lend Dean just enough arousal to get through it. Sam is _fucking_ him with his finger. He's got Sam's finger inside of him, and he's going to have a whole lot more if he can get a grip. Dean curses low under his breath and while he's not quite as hard as he was before, Sam fixes that. He doesn't insult Dean by going slow and steady; there's an intent behind each thrust of his finger. Dean doesn't even realize he's started to relax at first, not until Sam suddenly gives him an added warning.

His confusion lasts only until he feels the second finger press into his hole, and that's when Dean finally hisses. _That_ stings a little, but it's kind of a good sting. It's memorable. It's _Sam_ , and so Dean pushes back, letting his legs spread just a little as Sam fucks into him with his fingers. He's quicker this time, letting Dean feel first and adjust later, and there's something just fucking _good_ about that. Dean chews at his lower lip, breathing rough, but when Sam just up and says what he does, that's when Dean finally groans a low, " _fuck_ , Sam," and lets his head fall back on the pillow. His cock aches, and maybe it's really fucked up, but this is hot. Maybe tomorrow they'll all go up in flames. Maybe they'll all die bloody, but at least he has this, has Sam. 

Dean rolls his hips on a punched-out exhale that turns into a rougher curse when he feels Sam's knuckles against his rim. "Yeah... yeah, you are." It should be humiliating, but it's not. Somehow hearing Sam talk makes this easier. Dean wets his lips and manages a quick grin. "Tell me how you're gonna fuck me. You want to, right? You get off on talking dirty?"

* * *

Sam's always liked dirty talk. It must be a Winchester thing because he knows Dean does too. Christ, he's _heard_ Dean go at it... He'd been seventeen at the time and he'd heard Dean murmuring all the filthy things he was going to do to a waitress he'd managed to hit it off with. Dean's hand had been slipping under her uniform skirt when Sam had spied them getting a little more familiar with each other. Sam hadn't lingered too long (he wasn't a creep back then at least) but he'd _heard_ his brother's tone, he'd picked up the words that sounded like a promise... 

He may be quite invested in this, but Sam is still paying attention for any indication that Dean wants him to stop or slow down. He's not that much of a deviant that he would dismiss any signs. Dean hasn't noticeably clenched down or tried to lift away from him, so Sam is taking it as a good thing. He knows from experience that it _does_ feel weird, but it's also a mindset thing too. Jess had been interested in trying out pegging and he'd been all gung-ho for that, completely at her mercy and so turned on through the whole process... but during another incident with her and a few close friends, Sam hadn't been interested in anyone playing with his ass and it had pretty much sucked. 

Dean's answering groan has Sam's head snapping back up to watch his brother. Sam's eyes are wide and excited as he witnesses Dean's hips move. When he sees Dean's tongue slide out to wet his lips and that playful trademark Dean-grin directed at him, Sam's feels his cock twinge. And then Dean goes one step further and invites him to _go on_... Sam has to swallow past nerves. He lets his free hand reach and trail down Dean's stomach, half because he wants to and half to once again remind himself that this is real. He's really doing this... 

"Yeah... Yes, I do," Sam answers, and there's an annoying earnestness to his voice that even _he_ can pick out. His hand wraps around Dean's dick, wanting to make sure it stays hard and keeps things a little more familiar. Sam strokes it slowly as his fingers move faster, the slick sounds only turning him on more. 

"Not going to let you hide, Dean. I'm going to watch you the entire time I fuck you. I'm going to look at your face as I slowly push inside of you... Or maybe I'll have you on top -- you want that? I'll hold your hips as you sit down on my dick. Keep you nice an' steady as I fill you up." 

It's then Sam purposefully crooks his fingers inside of Dean's ass and searches for a certain special gland.

* * *

To Sam, the earnestness is annoying. To Dean, it's endearing. Just for a split second amidst the noise and impending darkness, he sees Sam's near-hopeful expression, sees the way Sam's hand slides over his abdomen as his fingers fuck into him in short, quick thrusts that have Dean panting. And he sees _Sammy:_ earnest, dweeby, excitable, and eager to please. The sight sends something warm through Dean's chest and it immediately reminds him of times long-past. 

Quick moments stolen when they'd been traveling with Dad. Dean breaking protocol and bringing Sam a book or a game he'd been after, or just taking Sam out driving somewhere he'd been dying to go. A night out in the park with stolen fireworks Dad never would have approved of, and Sam's answering cheering and laughter. Just for a second, _that's_ what Dean sees, and despite the edge of pain and awkward pleasure, despite how wrong all of this is, his grin softens into something else. Hey, if Sam's this eager to be able to talk dirty, Dean's not about to argue.

As it turns out, he doesn't really get a chance to either. Sam's fingers speed up just enough to make a difference, and as uncomfortable as it feels, it _is_ kind of hot in a super fucked-up way. Dean shudders and then suddenly his hips twitch up almost like a goddamned conditioned response. Sam's giant hand is just suddenly wrapped around his dick and as weird as the feeling of fingers pushing into his ass is, the hand on his dick is familiar. Dean curses, hips stuttering in a way that means Sam has to compensate with his fingers but Dean doesn't care. That's more like it. Pleasure jumps up through him and suddenly all the discomfort takes a different, odd edge. It's good though.

It just gets better when Sam starts to talk. His voice is low, rough, and Dean knows he'll be able to hear this in his memory for decades. The thought of being on display, of Sam watching so closely as he fills Dean up is almost too much, almost impossible to handle, but that's what makes it good. Dean groans, breathless, nodding lazily because fuck, he'd do anything Sam asked if he just said it like that. But the thought of straddling his brother, of lowering himself down while Sam watches is just filthy enough that Dean squirms, his cock throbbing in Sam's hand. 

"Fuck. Fuck, yeah, want you to fucking watch me, Sam." 

The concept of not being able to hide is almost too much but Dean chases it anyway. He doesn't want to hide from this. He wants the discomfort, wants to remember this in every way he can. Before he can voice that, though, Sam's fingers twitch. Initially it's uncomfortable, but then Sam hits something, something that makes Dean feel like he's suddenly got to piss just as bad as it makes him feel like someone's just started jerking his dick from the inside. 

Dean's shout is only just bitten off and one of his hands grabs at his own mouth. He remembers Bobby and Cas in the adjacent room and screws his eyes shut, but there's an insistent rock to his hips when he pushes back. It doesn't take long for the urge to piss to abate, and then it's just _good_ , pleasure turning into a restless sort of itch under Dean's skin as he groans.

* * *

He may have known that he's been a little too interested in Dean for years, a little too in love, but Sam's never really fantasized about _doing_ anything specific. He at least had that much self-restraint. He'd tried to repress it, to push it down, ignore it. Be a Winchester about it. Now it feels like he's making up for lost time. Sam wants to think, consider, and babble out every last thought concerning what he wants to do with _and_ to Dean. He wants to hear Dean respond to each dirty whisper. He wants to see Dean's reaction. But they don't have time. There's no way to do it all, to do everything that is shooting through his head.

Sam feels like he's at some buffet and he wants to try every item, but there's not enough time nor is his stomach that large. He wants, he needs, more, more, just a bit-- and the seconds tick on, becoming minutes, becoming hours and this is his last night and he's tumbling into this, wanting to drink up every feeling and thought and knowing that there's no way he can process it all. 

In this moment, his one hand wrapped around Dean's dick stroking lazily, his fingers pumping into Dean's ass, Sam is as present as he can be (which isn't as much as Dean deserves, not nearly enough). Sam can't help but think about tomorrow and what he's signing up for, and what if he can't-- (but no, he can, he can). What about Dean? Would Dean stick to the promise? Would Dean get into trouble? 

But focusing on the dirty talk, on the fantasies, on the fucking, is far better. Sam tries to let it consume him, let the desire overwhelm him. When Dean says that he _wants_ to be watched, Sam feels his own arousal kick up a notch. He has to lick his lips and take a deep breath while actually thinking about the correct motion for stimulating the prostate. Thankfully he succeeds, Dean's expression and vocalization intense and perfect. Sam relents a moment and just watches his brother -- closed eyes, hips rocking, the groaning. It's hot. It's beyond hot. He wants to have Dean begging, Dean broken down from the pleasure, Dean writhing... but there's no time. Sam doesn't even think he could manage to wait and do all of that. (He's been waiting for so many years anyway.) 

"You're perfect like this," Sam murmurs, his voice warm and velvety. His finger go searching again, rubbing lightly at Dean's prostate before ceasing and just thrusting in normally. "So perfect for me, Dean. Letting me finger you open." Sam adds another finger carefully, his other hand quickening on Dean's cock to ease the transition. "Almost there, almost ready for me to fuck you."

* * *

This isn't the first time Dean had had a finger up his ass, but this is the first time he's really liked it. Maybe it's because he's in the right mindset for it, maybe it's because he's just so fucking desperate for everything to be _okay_ that he throws himself into the moment, feeling every twist of Sam's finger. Or maybe it's simply because it's Sam. Both because he's a guy and so clearly he has a fairly good idea of what guys like, and because it's _Sam_. His brother. His... fuck, his world.

Dean feels the edge of something that feels like a scream begin to threaten him and then suddenly Sam's finger is curling and that same lance of deep pleasure hits him. Dean grunts, head tipping back on the pillow, hips awkwardly hitching like he's not sure whether to thrust up into Sam's fist or fuck himself back on the fingers up his ass. It's not something he has much experience with and the reality is enough to make his breathing hitch. 

Sam's praise, when it comes, goes straight to Dean's chest. There's a touch that goes to his dick, making it throb in Sam's hand, but the rest of it hits Dean hard. Sex and approval go hand-in-hand and as much as a part of him wants to dismiss Sam's praise (he's the big brother; Sam isn't supposed to praise _him_ ) the rest of it just lodges like hooks under his skin. Dean groans low, the muscles of his abdomen flexing and shifting, and as Sam's fingers press in deep again, Dean lets himself relax. He doesn't even make the decision to do it. He just does it. It means Sam's fingers have an easier path and it means the tension keeping him in his own mind fades just enough for the next rub to his prostate to have Dean's lips parting on a silent gasp, a small bead of precome seeping out to rest, incriminating, at the head of his cock. Dean curses, voice rough as if the complete opposite of Sam's warm, velvet tone. 

"F-fuck, man. Yeah, that's... fuck, never thought that'd sound so fucking good."

The reality of the moment seems so impossible. Sam is going to fuck him. His little brother is going to fuck him. Had Sam's fingers not already been in his ass, Dean isn't sure he'd have been able to register what that meant. But as it stands, as Sam's fingers thrust and his hand strokes, Dean hisses and spreads his legs a little wider as two fingers become three. It burns but it's a good burn. Still weird but not bad-weird. It's exactly the level of different that he needs, and before Sam has even started to thrust again, Dean pushes back, forcing Sam's fingers in deeper with a rough curse. 

"Come on, Sammy," he pants, feeling oddly wired, a restless energy under his skin. "I wanna remember this. Wanna feel it."

* * *

Sam's pupils are blown with lust, eyes focused as he watches each and every reaction Dean makes. He takes all of them in; he delights in seeing Dean's hips lift off the bed, he enjoys seeing Dean's stomach clench, he relishes in feeling Dean's body steadily grow receptive to his fingers. Sam watches Dean's mouth part in pleasure and his own lips pull into a satisfied smile. Being the direct cause of all of these reactions is absolutely thrilling.

He still can't believe all of this is happening, that Dean kissed him back, that Dean let him do _any_ of this. Dean had the gall to say it was okay, that _he_ was okay... It somehow seems less believable than the idea of the friggin' Apocalypse. But here they are... Dean is naked, his cock hard and leaking a little and his ass being stretched open. And yeah it's messed up, of course it is, but there's also love and trust here. There's just gotta be.

Three fingers deep, it's going to be happening soon. God, Sam is far too excited at that knowledge. When Dean pushes back and simply encourages him, Sam can't help but groan. And then Dean's words - _'I wanna remember this. Wanna feel it'_ \- threaten to almost ruin the whole thing. But he's too much of a freak to stop now. Even if Dean is just doing this to appease him, to have one last 'Sammy is a freak' memory, Sam can't back out now. 

"You will," Sam says. "Promise." With that, he pulls out his fingers and removes his hand from Dean's dick. He briefly considers going for a condom... But why bother? He's sure they're both "clean" in that regard. Dean had been the one to give him the safe sex talk anyway. 

No. He wants to feel Dean as much as he can. To rip away any last barriers between them. So, Sam finally peels off his boxers, his dick happy for the freedom now. He throws them to the floor and goes for the lube, squeezing some out on his fingers and slicking up his cock. 

"Move over," Sam instructs and Dean complies. Sam crawls to the headboard, placing a pillow up as he sits his back against it. Maybe having Dean sit on his cock is not the most practical or easy position for a first time, but Sam wants to be able to look at him and hold him. 

"Come here," Sam beckons, a small excited smile on his face, his hand outstretched to help Dean if needed.

* * *

Getting fingered open isn't exactly a graceful experience, but it isn't a bad one either. It's uncomfortable and awkward, feels weird, but when Sam's three fingers curl, Dean swears that the sparks he sees behind his eyes are real. What had started out as uncertain has become a need, and as much as Dean's going to freaking hate himself for this later, he still does it. He still arches his hips and takes Sam's fingers in, wide and deep and so much more than he's ever had inside of him before. It takes them a while to find a rhythm that Dean doesn't fuck up because he's not used to being on the passive end like this, but it feels good when he finds it, and Sam fucks his fingers in until Dean feels like if he doesn't get a hand on his dick soon, he's going to explode.

So when Sam suddenly pulls out his fingers, Dean bites back what would have been a very embarrassing sound and, reeling, lets himself relax back against the bed. He's panting, flushed, his eyes dark and his lips well-bitten, and he feels like Sam's just ripped the rug out from under him. Dean's left watching, half-confused, half-nervous as Sam's hands move to his boxers, but Dean can't quite mask his expression when Sam's suddenly naked. 

He tries to tell himself it's nothing he hasn't seen before, but the knowledge that Sam is, uh... _proportional_ is enough to both twist his stomach and make him feel even more determined. Dean wets his lips, kicks his nerves in the ass, and he swallows them down as he rolls out of the way to make room for Sam. Moving feels really fucking weird; Dean isn't sure he likes the way lube feels on his ass. 

It's too slick, too uncomfortable, but he doesn't complain. He just watches as Sam settles back against the headboard and reaches for him. Dean only hesitates for a second before he moves, doing as he's told. Even as he moves over and awkwardly finds his place on Sam's lap, straddling his hips, he has the feeling that had the situation not been so dire, had this not been the end of the world, Dean would have let himself be a little more fixated on Sam's impossible dick. As it is, he can't _entirely_ drop it. 

"Christ, Sam. Little baby nerd brother, my ass," Dean says, and then (realizing the unintentional joke) he snorts a soft laugh that's probably more nerves than anything. "You cocky bitch."

Grinning seems impossible now, but he can't quite shake it. His heart is pounding and he's pretty damn sure that there's no way that _that_ is going to fit inside of him, but whatever. He'd wanted memorable, and he's got memorable. 

One hand shakily bracing itself on Sam's shoulder, Dean squirms a little closer and then reaches back. It strikes him as he wraps his hand around Sam's dick that he's not actually touched him properly before now. Dean's a little rankled about that, but seeing as he's currently spreading his legs and pressing the head of Sam's cock up against his ass, he decides Sam's probably going to forgive him. Dean's teeth catch on his lip and his pulse speeds up even more, but when he starts to ease himself back and feels the beginning of a real stretch, he doesn't care. This is Sammy, and Dean wants this. 

* * *

Sam knows he's not lacking in the below the belt department. He also knows men can be rather finicky about sizes (not that Dean should be concerned). It's still amusing to have Dean point it out and then sort of insert his foot into his mouth right after. Sam wants to point out that nerds can have big cocks and he hasn't bragged about his junk, thank you very much, but Dean is in his lap, naked... and somehow calling him a jerk or any other of the silly names that they call each other is right out of his mind. Not important. No time.

He's going to fuck Dean. Sam can't even begin to imagine what horrible expression is on his face -- eager, desperate, aroused? Some mix of all of the above probably. Dean's grin is a little off, but Sam isn't going to ask him if he's all right. It's not time for some heart to heart (not that Dean would ever admit to _not_ being fine anyway. They're both not fine, how could they be? They haven't been fine for a while.)

Sam's hands have instinctively grabbed onto Dean's hips to steady him and then he feels Dean reach between to hold his cock still and Sam's has to swallow past his nerves because _oh, God_ , Dean is going to - Dean _is_ sitting himself down on his cock - and Sam struggles to remain perfectly still as he tries to support his brother as best as possible. It's pretty damn difficult because Dean is blissfully tight, his body like a vice and Sam knows the head of his cock will be the worst of it. But Dean presses on and slowly works himself down and Sam's breathing is labored, his hands holding far too tight. When the tip of his cock pushes into tight welcoming heat, Sam can't help but moan and let his head fall back against the headboard. 

"Wow, Dean," he mumbles. "You feel amazing. Just... Just no rush." Oh, _he_ wants to rush, to snap his hips up and bury his dick deep inside but he'll wait. Sam raises his head and he smiles at his big brother. Feeling a storm of pleasure and emotions, he carefully leans forward to nuzzle at Dean's chin. "So fucking good. I want to feel you more."

* * *

There are a million things that Dean should be saying. He feels like begging (for pleasure and for Sam to change his mind), feels like screaming (in frustration and hopefully in pleasure eventually), and in the back of his mind he's got this dumb-as-fuck notion that he should remind Sam about safe sex. But just like he doesn't beg, or scream, Dean doesn't stop and ask Sam to put on a condom. It's risky but he doesn't care. Sam's still Sam, and he trusts that Sam has been safe all along. Even if he hasn't been, does Dean even care? No. It's dumb, but he doesn't give a fuck. He's getting one. (Not even the mental joke is enough to really shove away his nerves.)

It doesn't matter in the end, because thoughts of the next day are quickly secondary. Thoughts of condoms don't matter. Instead Dean's world is quickly narrowed down to the vice-like grip Sam has on his hips and the blunt pressure slowly growing more and more pressing. It starts out weird and quickly passes the point into uncomfortable, but Dean doesn't stop. He's not the one with his cock sinking into a tight hole, but his breathing is still ragged as he shifts closer, as he pushes himself. The grip on his hips quickly turns from bracing to bruising but Dean just grunts a soft sound of satisfaction and presses into the bruising grip enough to feel Sam's thumbs dig harder into his hip bones. 

He'll bruise, but he wants to. And though the way Sam's dick slowly presses into him is quickly turning from uncomfortable to painful, Dean doesn't stop. Even if he'd wanted to, the expression on Sam's face would have spurred him on. Sam's breathing is more labored than his own, and Dean wants to chase the flush down his neck to see how far it goes. He feels a little hysterical as he pushes himself, his pulse racing, his muscles protesting, but Sam's expression of desperation is really freaking hot. (And something he wants to remember. Fuck, he wants to remember this.)

When the head of Sam's cock finally sinks into him, Dean can't quite bite back the hiss forced out of him. Immediately the sensation is too much but not enough. Dean isn't sure if he feels aroused or panicked or wired, but he guesses it's some mix of the three. It stings despite Sam's care, and that makes sense. Anal's not really something Dean tries with someone who's never done it before, but _fuck_ if this isn't what he wants. 

Shuddering, sweat pooling on his skin from sheer overwhelming sensation alone, Dean almost collapses forward onto Sam but holds himself back. He feels raw, and he's honestly intending to just wait on the whole damn thing... but then Sam's moan registers. Then Dean catches a look of the pleasure, the flush to Sam's skin, and the way he's holding himself back, and the knowledge that Sam's giving him an out to rest (pussy out) hits him low.

Jaw setting, hand gripping at Sam's shoulder, Dean bites out a series of emphatic curses and then braces himself again. He pushes back, not all at once - he's not _insane_ \- but fast enough to really feel it. Dean's breath all but chokes out of him and there's a definite tremble to his body as he sinks down on Sam's cock, but he pushes until it's halfway in and then shakily takes his other hand away, grabbing at Sam's other shoulder. 

"Fuck, _fuck_ ," he hisses, tense. "Feels... I don't know. Just a lot of it." Good, bad, Dean doesn't know. He doesn't really care. He just leans in to press his forehead to Sam's shoulder and shudders. "Give... give me a minute. Then you can move again."

* * *

He's going to Hell and maybe this is just another nail in his coffin, another strike against Sam Winchester, boy with the demon blood. It might not be a commandment, but he's pretty freakin' sure messing around with demons, releasing Lucifer and fucking his brother are 'go straight downstairs' worthy anyway. No passing Go, no collecting $200. He doesn't want any obituary, no gravestone or cross (they've buried enough family). Monsters get locked up and maybe he's no wendigo or werewolf, but he's messed up enough to deserve the cage too. 

And he proves it right now because he shouldn't be asking Dean to do this and he shouldn't be making Dean sit on his fucking cock either. Sam can see the tension, can feel it, and he knows he's not going to stop Dean. He can't. He's committed to this wretched decision. Right now he doesn't even know if the sex is the worst part of it (of him). Surely it's his own pit inside, something dark and carnivorous, a twisted desire to have and consume, to hoard away and not share. It's nothing to be proud over. It's not good and wholesome. 

And seeing Dean's discomfort, hearing the hiss of displeasure should knock some sense into him, but it doesn't. First time is the worst/weirdest and it would have been better to go up to a dildo next, but Sam kind of likes being the cause. It's a sick antsy sort of excitement that Sam feels a little ashamed of, but dammit he wants to leave a mark on Dean. Cas had, after all. 

He sees Dean's jaw go tense and for a moment Sam is a little confused why Dean is pushing himself, but then he clues in.... Dean never likes care or taking it slow or easy, so why would he here? Bit by bit Dean lowers himself more onto Sam's cock and Sam is engulfed in a perfect sweltering tightness and heat. His muscles tense and Sam is panting, his eyes wide as he focuses only on Dean -- every detail, every flicker of expression. And when Dean leans in, resting against his shoulder and admitting that he needs a moment, Sam just laughs softly. 

"Take it easy, man," he whispers, head tilting down to kiss Dean's hair. When Dean seems to relax a little, Sam dares to pull Dean down the rest of the way. It's intense and shocking and he feels a little winded now fully sheathed inside of his brother. Sam all but clings onto Dean, arms wrapped around his torso and pulling him into a hug, Sam doesn't move. All he wants to do is jackrabbit into Dean, fuck him fast, but Sam pulls himself back from the edge. Not like that... 

"Dammit, Dean," Sam gasps, fingernails digging into Dean's shoulder blades. "So good, so damn good I can't even think of another word for 'good '"

* * *

Dean says a minute and he means a minute. They don't have the luxury of time. Maybe if they'd done this sooner, Dean would have asked for longer (unlikely, knowing him) but as it is now, his body's just going to have to catch up. He clings to Sam's shoulders, and he's embarrassed as all Hell that he needs to, but he'll deal. Each breath feels like it's being shoved out of him, heavy and labored, like Sam's cock is pushing it out, but Dean doesn't struggle against it. 

He does what he can to breathe, to relax, to grind his forehead in against Sam's shoulder and curse as he tries to figure out how to handle this much sensation all at once. Dean's died before; he can remember the rending agony and coldness and heat, but somehow _this_ still feels like more. Maybe it's because it's just pure sensation, good and bad, or maybe it's just because it's Sam.

He isn't sure a minute's passed by the time Sam's hands tighten on him. Dean had focused hard on the feeling of Sam laughing against him and maybe he'd wasted seconds thinking about it, but the fact is that they're gone now. So when Sam's hands pull him down and Dean feels _more_ , he begins to gasp, then changes his mind and just groans instead. It feels freaking impossible, like every second has to be _it_. The end, no more, all in, but it doesn't stop. Dean's got a Hell of a new respect for the women who've ever let him do this, but for the life of him, he can't remember a single one right now. 

All he can feel is Sam. Sam's arms, the way the hair on Sam's legs catches on his own, the light graze of stubble, the solid muscle under his hands, every little hint that this is _Sam_ and not someone else. He feels strung out by the time his ass finally presses against Sam's thighs, and the curse he lets out is hissed, awed, because, _fuck_ , he did it. How the Hell...

Sam's arms move then, all but crushing Dean into a hug, and Dean gasps at the pressure and the way his cock drags wet along Sam's stomach. He's not as hard as he was, but Dean's amazed he's even sporting a semi after that. It's got to be Sam. Sam helping him distract himself, Sam's gasping, everything he says... there's no denying that it's hot. Dean feels a little drunk on it, on the bite of nails in his skin and the way Sam sounds. He bites his lip and though he still has no idea what his body even _wants_ right now, he rolls his hips, feels a spike of sensation, and decides that it doesn't really matter if it's good or not. It's overwhelming, and it's Sam. It's perfect. 

" _Oh_ , fuck... Christ, then don't. 'Good' is... is good, Sam. It's good. _God_ , you're deep." It strikes him after he's said it that he's heard women say that to him. He's never really understood that feeling until now. Now Dean gets it. "Fuck, Sam. You wanna scratch, scratch. It's okay," he gasps, rolling his shoulders into the bite of Sam's nails as he circles his hips again, a little quicker, like Dean's given himself permission for a set number of moves to get used to this before he throws himself in, ready or not.

* * *

It feels like some fevered dream. How can this be Sam's life? Both naked, clinging to each other, Dean seated on his dick and his life forfeit tomorrow... Sam has no clue how he's supposed to process any of this. Yeah, they've never had any semblance of a _normal_ life, but this goes the extra mile and then some. Once again, Sam is glad that he won't be here to face the consequences. Dean is going to have to look at Bobby and Cas while he... He gets to dance with the Devil and burn. But it's all right. Better than an all-out war here on Earth. This is something he can do and be proud about. Hopefully Dean will be proud too, God only knows how many wrong decisions he's made...

But this is far better than anything he's done before. Better than the high of demon blood and Ruby, better than Jess even, and yeah it's so messed up but Dean is his own blood. Dean is the single person that knows him better than anyone else, that's seen him at his worse and loved him despite it. His own brother went to _Hell_ for him -- a sacrifice that he can repay tomorrow to ensure Dean has a better ending. He doesn't like to think about it, how Dean is his everything. Dean has been with him through it all. Through the thick 'n thin and the idea of separation... It's a thought Sam can't even begin to deal with, but it's going to happen. It's inevitable.

But now Dean's here with him here, shaking and bearing it. Sam wishes he could find the words for everything that's inside his head and heart because this is his last chance and even if Dean hates mushy crap, shouldn't he say something? His vocabulary fails him. And Dean rocks a little bit and Sam can only groan as pleasure pierces through him, hot and consuming, and it feels far too intense. Hearing Dean comment on him being deep is about the hottest thing Sam's heard and his eyes shut tightly and he obeys. He rakes his nails down Dean's back, shifting his hips a little to feel Dean better as he scratches at muscle. 

"Goddammit," Sam grits out and his hold relaxes a little, his hands then sliding down to Dean's hips. "Move when you can, wanna watch you fuck yourself on my cock," Sam says.

* * *

The feeling of Sam's nails digging into his skin and dragging down is so sudden and so sharp that Dean has to consciously keep his voice down as he groans. He almost forgets about Cas and Bobby in the other room for a moment, but the last second serves as his (somewhat embarrassing) reminder. Dean can't help but be stuck on the sting to his back because it feels good. He likes sex being a mix of sensation, pleasure and pain. 

Dean isn't sure he's ever felt satisfied with a fuck without bruises pressed into his arms, or hickeys everywhere, or a hand in his hair and tugging. Nails on his back might be one of his favorites, but it's so much different like this than how it feels when _he's_ the one doing the fucking. It still rips through him like a knife, though, still leaves him aching. 

A lot leaves him aching though. Not all of it good. Dean's doing what he can to keep his mind in the moment, to focus _here_ , on what's happening to him now. He doesn't want to think about tomorrow, doesn't want to so much as let the thought touch him because he knows he's only got so much of a game face to fall back on. One slip and he's down for the count and begging. Dean swallows it back, forces himself into the moment, and Sam helps by shifting his hips just enough that when Dean moves again, pleasure flares bright behind his eyes. 

Dean gasps, a silent, hollow sound, and his own nails bite into Sam's shoulders. He feels the answering burn on his own back and some visceral side of himself hopes he's bleeding.

"Yeah," Dean manages to choke out, voice slightly muffled by Sam's shoulder. "Yeah, I got it." He'll move when he can. Right now it feels like he doesn't have much strength left in his legs but he's determined. 

Dean's breathing is rough and ragged as he struggles to relax. It still feels weird as all Hell and it definitely still stings, but there's an odd mix of pained pleasure in the whole thing and he silently admits to himself that he likes this. Guiltily, he likes it even more because it's Sam. Dean isn't sure he'd let this happen with anyone else. So when he feels too restless, when he's aware of how long he's been still, Dean finally sucks it all up, leans back away from Sam's shoulder, and begins to move. 

He's a little sluggish and awkward, lifting himself up and feeling the weird drag of sensation as Sam's cock slides halfway out of him before Dean drops back down. It's still a lot, a crazy level of sensation, but his dick's not soft and it feels good. He lets out a shaky groan and tries not to close his eyes as he rocks his hips instead, moving them in slightly more familiar circles that succeed in Sam's cock grinding in deep. Given the way his breath catches, it feels fucking amazing.

* * *

Should Sam have acted on this before? Said something? Tried _something? Anything?_ Would Dean even have allowed it? Somehow Sam thinks it'd be a big fat no. Sam knows that Dean is only going along with this because of what's happening tomorrow, because he'll be going away. That is, if he manages to succeed.

But has to. He freakin' has to. This is Sam's one chance to make it up to everyone. To Dean. To Bobby. To Cas. The whole _world._ He _has_ to make it better. Dean may have technically broken the first seal, but Sam had broken the last and let out Lucifer. He can fix this -- although it might break Dean in the process. Funny how they can be so resilient and yet fragile at the same time. Right now, Sam doesn't feel very resilient, he feels like he's crumbling, but if he holds on to Dean, just maybe...

So he rakes his nails down Dean's back and Sam wonders if Dean likes the pain because it's pleasurable or because it's what he's used to. Dean has staunchly never went into all that many details about his time in Hell and Sam, wisely, has never pushed for it. Guilt is a powerful enemy, it's one that neither of them seem to be able to shake off. But Sam doesn't want to think about Dean possibly thinking of this as some punishment. Because Dean's weight on top of him is just right and Dean's body is the perfect mix of _hot_ and _tight_ that threatens to push Sam over far too quickly and he doesn't want this to be over so soon. 

Sam doesn't dare to rush Dean. He lets his brother take the time to adjust and get his bearings because he knows this is overwhelming and likely uncomfortable, but Dean is still with him, straddling him and sitting on his dick and Sam isn't abandoned. It means _everything_ to him right now and Sam knows the dirty talk will always be easier, will likely be preferred, but this is his last night on Earth with his brother and it almost feels disingiune to just go there again. 

Dean raises his head away from Sam's shoulder as he lifts himself up to fuck back down and Sam shudders. He clenches his jaw to not move, to not betray Dean but when Dean rolls his hips, Sam's hands slide up to the back of Dean's head and he pulls him in for a kiss. It's more desperate than dirty and Sam flexes his hips just a little, feeling the perfect hot clench around his cock.

* * *

Dean's not used to feeling clumsy in bed, but right now, he doesn't really have a choice. Sam might have claimed some experience with this sort of thing, but Dean's never had any before. He knows how to fuck, knows how to move his hips to make his partner feel the best, and how to drive into someone and reap the benefits of pleasure for himself too, but this is new ground for him. Dean doesn't know how to wrench pleasure out of this for himself, and he isn't sure how to move his hips to give Sam what he deserves. But he must be doing _something_ right, because Dean can feel the hot throb of his brother's dick in his ass (which is a feeling he can't even begin to explain) and given Sam's grip on his hips, it has to feel good even if Dean doesn't know what he's doing.

For an overwhelming moment, he thinks about what women do to him when they're riding him, but the memories feel like sand sliding between his fingers. Dean's mind is too wired and shattered. All he can think of is this, because if he lets himself think about more, he doesn't think there's any way that he _won't_ think about tomorrow. So he throws himself into this, overwhelming and awkward as it is. He rolls his hips and feels the grind of Sam's cock, feels the bite of nails digging into his skin, and he can't help the raggedness of his breathing as he grabs at Sam's shoulders. He wants to do this right. He wants to do one fucking thing _right_.

So when Sam's hands slide up to the back of his head and pull him in, Dean goes without protest. Somehow kissing feels like the only thing he _can_ do as he rolls his hips, feeling each thick drag of Sam's cock over areas that have never been touched or stretched or filled like this before. Sam kisses him desperately and Dean's broken curse dies in his throat as he leans into it. It's messy and graceless, and he buries the fingers of one hand into Sam's hair to hold on, but it's _something_ that he can focus on. 

But when Sam's hips flex, when Dean feels the extra friction that _he_ hadn't caused, he tenses with a muffled hiss and rocks a little, trying to replicate it. Sam wants him to ride, and Dean's not going to let him down. Not like he's let Sam down before. He's going to do this right if it kills him. So despite the awkwardness and the sting, Dean breaks the kiss, braces his hand on Sam's shoulder, and rises up a little again before dropping back down. It feels clumsy to him, but it's a spike of sensation, and if he can make Sam feel good? He's going to.

* * *

It doesn't matter if Dean is clumsy or inexperienced in this. This stolen moment isn't about showing off skill or finesse and it's definitely not going to be bragging right or a shared story over a beer. Sam doesn't care if the pace Dean moves at is stilted or the fact that they both have their preferred styles of kissing. This is _real_ and this is all Sam has right now. Dean is with him and is going to be with him until the very end. 

Sam had erroneously believed that the end would be when they found Dad. He'd entertained the idea of going back to school. Sam had still held onto a small thread of hope that he wasn't actually getting sucked into the hunting life. But finding John Winchester hadn't solved anything, it had Dean and him losing their last remaining parent and then going on a hunt to kill the Yellow-Eyed demon. And any chance of a normal life had been thrown out the window when Dean sold his soul for Sam. How do you come back from that? You don't. Sam had fixated on trying to save Dean.

But Sam hadn't been able to do it. Sam had been helpless as Lilith pinned him to the wall and hellhounds ravaged his brother like he was simply a haunch of meat thrown to them. 

Powerless. Helpless. Weak. It's those feelings that had him turning to the demon blood. One misguided decision after another, this has been Sam's life. Killing Lilith had only broken the final seal and released Lucifer. Maybe one grand act isn't enough for salvation, but Sam isn't expecting any. He knows he's a lost cause. He's not sacrificing himself thinking that he's going to have an angel fly down there and rescue him after. This is a one-way ticket and Sam proves that that's where he belongs because he's fucking Dean.

Pleasure burns low and as good as it feels to have Dean riding him, Sam knows he needs something more. There's a desperation lancing through him, some dark twisting thing and he takes action. 

"Hang on," is the only warning Sam gives before he leans forward and pushes Dean onto his back. Sam is careful to not slip out as they change positions, Sam over top Dean now and getting onto his knees as Dean's legs curl around him. He takes Dean's wrists in his hands and pins them on the mattress, using them as an anchor point to push back on as Sam then begins thrusting both faster and harder. The shitty headboard creaks from the sudden motion and Sam's hair threatens to fall into his face, but he tries to shake it back as best he can. His eyes are locked in on Dean's face beneath him and there's definitely the sound of skin slapping against skin increasing. 

"Dean... So perfect, god, you feel perfect," Sam murmurs. He hadn't wanted to lapse into the dirty talk but maybe it's just easier than what else may slip out. "Nice and tight for my dick," Sam continues on, his voice strained. "How does it feel to have your virgin ass pounded?"

* * *

How many women has Dean had like this? How many times has he encouraged and touched and watched as a woman rolled her hips and put on one Hell of a show for him? He'd always found it hot, had always murmured praises and repeated consistently that his partners had been sexy, but now that _he's_ the one on this end of it, he wants to kick his past self for being so obvious, for not specifying or praising _more_ , because this is fucking exposing. He feels seriously in over his head as he braces his hand on Sam's shoulder and tries to find a rhythm that works. 

It's a different, sharper, painful kind of pleasure and it's so damn new that Dean's not sure how to work with it. He feels uncomfortably full, which somehow translates to _perfectly_ full, but like fuck if his body knows what to do. Does he rock forward? Push back? Move his hips around? He doesn't know how to translate what he's feeling into orgasm, so after a few fumbling seconds, he abandons that goal. Sam. _Sam_ is what matters. 

Dean's already bracing himself to just go for it, to grit his teeth through any discomfort and ride his brother until Sam comes. But before he's so much as had a chance to brace his heels on the bed, Sam suddenly says something and then Dean's center of balance changes. He grabs instinctively at Sam's shoulders with a rougher curse, and Dean feels woefully off-balance. Then his back hits the bed and his legs move automatically, feet touching down at first on the bed, and then against Sam's calves. Dean starts, trying to catch up, but then Sam's hands take his wrists and press them down.

Dean turns his head, looking at the grip Sam has on each of his wrists at either side of his head. Still stunned, Dean glances back up at Sam, and he's halfway through trying to figure out what to say when Sam's hips draw back and Dean is sharply reminded that his brother still has his _dick_ inside of him. The first thrust has the bed creaking, and Dean can't help himself as he throws his head back with a gritted cry. Sensation zips so sharply through his body that he can't tell if it's pleasure or pain, but given the tight, swollen feeling in his own cock, he must like it. 

Whatever angle Sam has found apparently works, because as he snaps his hips and sets up a rhythm, it's all Dean can do to keep from squirming away. It's intense in a way he's not used to, his hands balling into fists and each breath stuttering and sharp. And through it all, there's Sam, looking down at him, watching as pleasure and pain and intensity carve their way through him. Dean feels like he could come from that alone.

It's simpler to take it, which Dean is grateful for, but the feeling is so damn sharp and Sam's words have his face all but flaming. Dean's cock throbs at the sound of them, though, so it's apparently doing it for him. He hisses sharply, his back arching, and even if he doesn't know what the real answer is, he knows what to say. 

He grits out a sharper, " _fuck_ , Sammy. S'good. I think? Fuck, it's a lot." Which is... an odd mix of truth and what Dean knows he's supposed to say. It's hard to keep on track with Sam fucking him like he's done it every day of his goddamn life.

* * *

Rough. Fast. Dirty talk. This is more like Sam's experience with Ruby. The realization isn't pretty; frankly, it's a reminder Sam could do without. He doesn't want this to be anything like the frenzied, guilt-ridden demon drinking times. Ruby had been a two-timing bitch who'd fucked him over royally in the end. Sam had turned to her, desperate and at a loss when Dean had gone to Hell for him. Even now that sounds like a terrible excuse, but hasn't his big brother always been the needle pointing north on the compass? Sam's sure Dean wouldn't have done it. (Sam likes idolizing his brother at times, though.)

Sex isn't going to help anything. It's not helping anything right now. Sam's pretty sure he's just tearing new gashes into Dean and he isn't the one that's going to have to stitch Dean up again. Bobby? Cas? Hopefully Lisa and Ben can help. Sam doesn't like the idea of abandoning Dean, but how could he face him after what's he done -- what he's _doing._ This isn't something you can laugh off or drink away. A terrible part of Sam craves this to scar Dean, for a mark to be left behind on his brother. If Sam has to go away, he wants something inescapable to stay with Dean.

So he fucks Dean hard and he pins his wrists. Sam drinks in his brother's responses, the vocalization, the heavy breathing, the knowledge that Dean is really feeling him so fucking deep, as deep as Sam can get. It all spurs Sam on. Dean doesn't look away from his eyes. Dean takes it and he even takes the fucking horrible filth that Sam's saying. Dean says _Sammy_ and Sam feels his resolve harden. He'll burn this moment into Dean, he'll tarnish his brother, ruin him for anyone else--

"Gonna come, Dean," Sam warns as he feels the build-up of pleasure near the tipping point.

It then tips and Sam feels like he's falling. It's a rush as he buries himself deep and comes, his cock pulsing and filling Dean. Pleasure and guilt and relief mix together and taste like blood in the back of his throat. Sam shakes as he lets himself collapse onto Dean, his hands no longer clasping Dean's wrists but searching out his hands instead as he forces Dean to lace their fingers together.

"I shouldn't-- shouldn't have..." Sam rasps out, his head tucked into the crook of Dean's neck (is he hiding from shame or hiding in a safe place?). All Sam knows is that his short life has been a lesson of _shouldn't_ and _should_ and this is no different. 

Tomorrow he's going to break the pattern. It might break Dean in the process, but the Winchester's finish what they start. 

They also seem made to be broken.


End file.
